JPWO2003062182A1 - Method and composition for stabilizing reduced coenzyme Q bottom 10 - Google Patents

Abstract

The present invention stabilizes reduced coenzyme Q10 useful as a food, a nutritional functional food, a food for specified health use, a nutritional supplement, a nutritional supplement, a veterinary drug, a beverage, a feed, a cosmetic, a pharmaceutical product, a therapeutic drug, a preventive drug, etc. Methods and compositions for doing so are provided. A composition comprising reduced coenzyme Q10, fats and oils (excluding olive oil) and / or polyol, which does not substantially inhibit the stabilization of reduced coenzyme Q10. Moreover, it is set as the reduced coenzyme Q10 containing composition containing reduced coenzyme Q10, polyglycerol fatty acid ester, fats and oils, and / or a polyol.

Description

で表される。上記式（１）において、ｎは１〜２９の整数を表す。Ｒはそれぞれ独立して炭素数２〜２２の脂肪酸残基又は水素原子を表すが、全てのＲが水素原子となることはない。すなわち、上記式（１）で表されるポリグリセリン脂肪酸エステルにおいて、脂肪酸残基の数は１以上であれば特に制限されない。
好ましくは、ポリグリセリン脂肪酸エステル中の脂肪酸残基の数／グリセリンの重合度との比が約１／４〜約１／２である。ここで、グリセリンの重合度とは、重合したグリセリンの分子数を表す。例えば、ジグリセリンモノカプリレートの場合、脂肪酸残基の数は１（モノ）、グリセリンの重合度は２（ジ）であるので、上記比率は１／２となる。なお、式（１）中に脂肪酸残基が２つ以上存在する場合は、それぞれの脂肪酸残基は同一であっても良く、異なっていても良いが、一般に同一であるものが入手の容易さ等の観点から好ましい。
上記ポリグリセリン脂肪酸エステルとしては特に制限されないが、還元型補酵素Ｑ_１０の安定性や吸収性を考慮して、ＨＬＢが、下限として、通常４以上、好ましくは５以上、より好ましくは６以上、さらに好ましくは７以上、特に好ましくは８以上であり、また、上限として、通常１２以下、好ましくは１１以下、より好ましくは１０以下であるものが好適である。
ポリグリセリン脂肪酸エステルの具体例としては、例えば、ジグリセリンモノカプリレート、ジグリセリンジカプリレート、ジグリセリントリカプリレート、ジグリセリンテトラカプリレート、トリグリセリンモノカプリレート、トリグリセリンジカプリレート、トリグリセリントリカプリレート、トリグリセリンテトラカプリレート、トリグリセリンペンタカプリレート、テトラグリセリンモノカプリレート、テトラグリセリンジカプリレート、テトラグリセリントリカプリレート、テトラグリセリンテトラカプリレート、テトラグリセリンペンタカプリレート、テトラグリセリンヘキサカプリレート、ペンタグリセリンモノカプリレート、ペンタグリセリンジカプリレート、ペンタグリセリントリカプリレート、ペンタグリセリンテトラカプリレート、ペンタグリセリンペンタカプリレート、ペンタグリセリンヘキサカプリレート、ペンタグリセリンヘプタカプリレート、ヘキサグリセリンモノカプリレート、ヘキサグリセリンジカプリレート、ヘキサグリセリントリカプリレート、ヘキサグリセリンテトラカプリレート、ヘキサグリセリンペンタカプリレート、ヘキサグリセリンヘキサカプリレート、ヘキサグリセリンヘプタカプリレート、ヘキサグリセリンオクタカプリレート、ヘプタグリセリンモノカプリレート、ヘプタグリセリンジカプリレート、ヘプタグリセリントリカプリレート、ヘプタグリセリンテトラカプリレート、ヘプタグリセリンペンタカプリレート、ヘプタグリセリンヘキサカプリレート、ヘプタグリセリンヘプタカプリレート、ヘプタグリセリンオクタカプリレート、ヘプタグリセリンノナカプリレート、オクタグリセリンモノカプリレート、オクタグリセリンジカプリレート、オクタグリセリントリカプリレート、オクタグリセリンテトラカプリレート、オクタグリセリンペンタカプリレート、オクタグリセリンヘキサカプリレート、オクタグリセリンヘプタカプリレート、オクタグリセリンオクタカプリレート、オクタグリセリンノナカプリレート、オクタグリセリンデカカプリレート、ノナグリセリンモノカプリレート、ノナグリセリンジカプリレート、ノナグリセリントリカプリレート、ノナグリセリンテトラカプリレート、ノナグリセリンペンタカプリレート、ノナグリセリンヘキサカプリレート、ノナグリセリンヘプタカプリレート、ノナグリセリンオクタカプリレート、ノナグリセリンノナカプリレート、ノナグリセリンデカカプリレート、ノナグリセリンウンデカカプリレート、デカグリセリンモノカプリレート、デカグリセリンジカプリレート、デカグリセリントリカプリレート、デカグリセリンテトラカプリレート、デカグリセリンペンタカプリレート、デカグリセリンヘキサカプリレート、デカグリセリンヘプタカプリレート、デカグリセリンオクタカプリレート、デカグリセリンノナカプリレート、デカグリセリンデカカプリレート、デカグリセリンウンデカカプリレート、デカグリセリンドデカカプリレート、ジグリセリンモノカプレート、ジグリセリンジカプレート、ジグリセリントリカプレート、ジグリセリンテトラカプレート、トリグリセリンモノカプレート、トリグリセリンジカプレート、トリグリセリントリカプレート、トリグリセリンテトラカプレート、トリグリセリントリカプレート、トリグリセリンテトラカプレート、トリグリセリンペンタカプレート、テトラグリセリンモノカプレート、テトラグリセリンジカプレート、テトラグリセリントリカプレート、テトラグリセリンテトラカプレート、テトラグリセリンペンタカプレート、テトラグリセリンヘキサカプレート、ペンタグリセリンモノカプレート、ペンタグリセリンジカプレート、ペンタグリセリントリカプレート、ペンタグリセリンテトラカプレート、ペンタグリセリンペンタカプレート、ペンタグリセリンヘキサカプレート、ペンタグリセリンヘプタカプレート、ヘキサグリセリンモノカプレート、ヘキサグリセリンジカプレート、ヘキサグリセリントリカプレート、ヘキサグリセリンテトラカプレート、ヘキサグリセリンペンタカプレート、ヘキサグリセリンヘキサカプレート、ヘキサグリセリンヘプタカプレート、ヘキサグリセリンオクタカプレート、ヘプタグリセリンモノカプレート、ヘプタグリセリンジカプレート、ヘプタグリセリントリカプレート、ヘプタグリセリンテトラカプレート、ヘプタグリセリンペンタカプレート、ヘプタグリセリンヘキサカプレート、ヘプタグリセリンヘプタカプレート、ヘプタグリセリンオクタカプレート、ヘプタグリセリンノナカプレート、オクタグリセリンモノカプレート、オクタグリセリンジカプレート、オクタグリセリントリカプレート、オクタグリセリンテトラカプレート、オクタグリセリンペンタカプレート、オクタグリセリンヘキサカプレート、オクタグリセリンヘプタカプレート、オクタグリセリンオクタカプレート、オクタグリセリンノナカプレート、オクタグリセリンデカカプレート、ノナグリセリンモノカプレート、ノナグリセリンジカプレート、ノナグリセリントリカプレート、ノナグリセリンテトラカプレート、ノナグリセリンペンタカプレート、ノナグリセリンヘキサカプレート、ノナグリセリンヘプタカプレート、ノナグリセリンオクタカプレート、ノナグリセリンノナカプレート、ノナグリセリンデカカプレート、ノナグリセリンウンデカカプレート、デカグリセリンモノカプレート、デカグリセリンジカプレート、デカグリセリントリカプレート、デカグリセリンテトラカプレート、デカグリセリンペンタカプレート、デカグリセリンヘキサカプレート、デカグリセリンヘプタカプレート、デカグリセリンオクタカプレート、デカグリセリンノナカプレート、デカグリセリンデカカプレート、デカグリセリンウンデカカプレート、デカグリセリンドデカカプレート、ジグリセリンモノラウレート、ジグリセリンジラウレート、ジグリセリントリラウレート、ジグリセリンテトララウレート、トリグリセリンモノラウレート、トリグリセリンジラウレート、トリグリセリントリラウレート、トリグリセリンテトララウレート、トリグリセリントリラウレート、トリグリセリンテトララウレート、トリグリセリンペンタラウレート、テトラグリセリンモノラウレート、テトラグリセリンジラウレート、テトラグリセリントリラウレート、テトラグリセリンテトララウレート、テトラグリセリンペンタラウレート、テトラグリセリンヘキサラウレート、ペンタグリセリンモノラウレート、ペンタグリセリンジラウレート、ペンタグリセリントリラウレート、ペンタグリセリンテトララウレート、ペンタグリセリンペンタラウレート、ペンタグリセリンヘキサラウレート、ペンタグリセリンヘプタラウレート、ヘキサグリセリンモノラウレート、ヘキサグリセリンジラウレート、ヘキサグリセリントリラウレート、ヘキサグリセリンテトララウレート、ヘキサグリセリンペンタラウレート、ヘキサグリセリンヘキサラウレート、ヘキサグリセリンヘプタラウレート、ヘキサグリセリンオクタラウレート、ヘプタグリセリンモノラウレート、ヘプタグリセリンジラウレート、ヘプタグリセリントリラウレート、ヘプタグリセリンテトララウレート、ヘプタグリセリンペンタラウレート、ヘプタグリセリンヘキサラウレート、ヘプタグリセリンヘプタラウレート、ヘプタグリセリンオクタラウレート、ヘプタグリセリンノナラウレート、オクタグリセリンモノラウレート、オクタグリセリンジラウレート、オクタグリセリントリラウレート、オクタグリセリンテトララウレート、オクタグリセリンペンタラウレート、オクタグリセリンヘキサラウレート、オクタグリセリンヘプタラウレート、オクタグリセリンオクタラウレート、オクタグリセリンノナラウレート、オクタグリセリンデカラウレート、ノナグリセリンモノラウレート、ノナグリセリンジラウレート、ノナグリセリントリラウレート、ノナグリセリンテトララウレート、ノナグリセリンペンタラウレート、ノナグリセリンヘキサラウレート、ノナグリセリンヘプタラウレート、ノナグリセリンオクタラウレート、ノナグリセリンノナラウレート、ノナグリセリンデカラウレート、ノナグリセリンウンデカラウレート、デカグリセリンモノラウレート、デカグリセリンジラウレート、デカグリセリントリラウレート、デカグリセリンテトララウレート、デカグリセリンペンタラウレート、デカグリセリンヘキサラウレート、デカグリセリンヘプタラウレート、デカグリセリンオクタラウレート、デカグリセリンノナラウレート、デカグリセリンデカラウレート、デカグリセリンウンデカラウレート、デカグリセリンドデカラウレート、ジグリセリンモノミリステート、ジグリセリンジミリステート、ジグリセリントリミリステート、ジグリセリンテトラミリステート、トリグリセリンモノミリステート、トリグリセリンジミリステート、トリグリセリントリミリステート、トリグリセリンテトラミリステート、トリグリセリントリミリステート、トリグリセリンテトラミリステート、トリグリセリンペンタミリステート、テトラグリセリンモノミリステート、テトラグリセリンジミリステート、テトラグリセリントリミリステート、テトラグリセリンテトラミリステート、テトラグリセリンペンタミリステート、テトラグリセリンヘキサミリステート、ペンタグリセリンモノミリステート、ペンタグリセリンジミリステート、ペンタグリセリントリミリステート、ペンタグリセリンテトラミリステート、ペンタグリセリンペンタミリステート、ペンタグリセリンヘキサミリステート、ペンタグリセリンヘプタミリステート、ヘキサグリセリンモノミリステート、ヘキサグリセリンジミリステート、ヘキサグリセリントリミリステート、ヘキサグリセリンテトラミリステート、ヘキサグリセリンペンタミリステート、ヘキサグリセリンヘキサミリステート、ヘキサグリセリンヘプタミリステート、ヘキサグリセリンオクタミリステート、ヘプタグリセリンモノミリステート、ヘプタグリセリンジミリステート、ヘプタグリセリントリミリステート、ヘプタグリセリンテトラミリステート、ヘプタグリセリンペンタミリステート、ヘプタグリセリンヘキサミリステート、ヘプタグリセリンヘプタミリステート、ヘプタグリセリンオクタミリステート、ヘプタグリセリンノナミリステート、オクタグリセリンモノミリステート、オクタグリセリンジミリステート、オクタグリセリントリミリステート、オクタグリセリンテトラミリステート、オクタグリセリンペンタミリステート、オクタグリセリンヘキサミリステート、オクタグリセリンヘプタミリステート、オクタグリセリンオクタミリステート、オクタグリセリンノナミリステート、オクタグリセリンデカミリステート、ノナグリセリンモノミリステート、ノナグリセリンジミリステート、ノナグリセリントリミリステート、ノナグリセリンテトラミリステート、ノナグリセリンペンタミリステート、ノナグリセリンヘキサミリステート、ノナグリセリンヘプタミリステート、ノナグリセリンオクタミリステート、ノナグリセリンノナミリステート、ノナグリセリンデカミリステート、ノナグリセリンウンデカミリステート、デカグリセリンモノミリステート、デカグリセリンジミリステート、デカグリセリントリミリステート、デカグリセリンテトラミリステート、デカグリセリンペンタミリステート、デカグリセリンヘキサミリステート、デカグリセリンヘプタミリステート、デカグリセリンオクタミリステート、デカグリセリンノナミリステート、デカグリセリンデカミリステート、デカグリセリンウンデカミリステート、デカグリセリンドデカミリステート、ジグリセリンモノパルミテート、ジグリセリンジパルミテート、ジグリセリントリパルミテート、ジグリセリンテトラパルミテート、トリグリセリンモノパルミテート、トリグリセリンジパルミテート、トリグリセリントリパルミテート、トリグリセリンテトラパルミテート、トリグリセリントリパルミテート、トリグリセリ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なかでも、ジグリセリンモノカプレート、ジグリセリンモノラウレート、テトラグリセリンモノラウレート、ペンタグリセリンモノミリステート、ペンタグリセリントリミリステート、ジグリセリンモノステアレート、テトラグリセリンモノステアレート、テトラグリセリントリステアレート、テトラグリセリンペンタステアレート、ヘキサグリセリンモノステアレート、ヘキサグリセリンジステアレート、ヘキサグリセリントリステアレート、ヘキサグリセリンペンタステアレート、デカグリセリンジステアレート、デカグリセリントリステアレート、ジグリセリンモノオレエート、ジグリセリンジオレエート、テトラグリセリンモノオレエート、ヘキサグリセリンモノオレエート、ヘキサグリセリンペンタオレエート、デカグリセリントリオレエート、デカグリセリンペンタオレエートが好ましい。より好ましくは、ジグリセリンモノカプレート、ジグリセリンモノラウレート、テトラグリセリンモノラウレート、ジグリセリンモノオレエート、ジグリセリンジオレエート、テトラグリセリンモノオレエート、デカグリセリンペンタオレエートである。さらに好ましくは、ジグリセリンモノカプレート、ジグリセリンモノラウレート、ジグリセリンモノオレエートであり、最も好ましくはジグリセリンモノオレエートである。
これらのポリグリセリン脂肪酸エステルを用いた場合には、上述したように、モノグリセリン脂肪酸エステル（有機酸モノグリセリドを含む）やポリグリセリン縮合リシノール酸エステル等を用いた場合とは異なり、還元型補酵素Ｑ_１０を油脂及び／又はポリオールの存在下、安定に保持することができる。
なお、本発明の組成物を食品用途に用いる場合には、上記のポリグリセリン脂肪酸エステルのうち、ポリグリセリン脂肪酸エステル中の脂肪酸残基が炭素数８以上、つまりカプリル酸もしくはカプリル酸よりも長鎖の脂肪酸であるのが好ましい。また、ポリグリセリン脂肪酸エステル中のグリセリンの重合度は１０以下であるのが好ましく、重合度が２のジグリセリン脂肪酸エステルがより好ましい。
上記ポリグリセリン脂肪酸エステルは、その共存・添加により、油脂及び／又はポリオールの安定化効果を阻害しにくいため、その含有量は特に制限されないが、例えば、補酵素Ｑ_１０を除いた系を基準として、下限は、通常１重量％以上、好ましくは２重量％以上、より好ましくは３重量％以上、さらに好ましくは５重量％以上であり、上限は、経済性等も考慮して、通常５０重量％以下、好ましくは４０重量％以下、より好ましくは３０重量％以下、さらに好ましくは２０重量％以下、特に好ましくは１０重量％以下である。言うまでもなく、必要に応じて、上記以外の量も含有しうる。
上記本発明において使用する油脂及び／又はポリオールとしては、食用又は医薬用に許容されるものであるのが好ましい。
上記油脂としては、動植物からの天然油脂であってもよく、合成油脂や加工油脂であってもよい。植物油脂としては、例えば、ヤシ油、パーム油、パーム核油、アマニ油、つばき油、玄米胚芽油、アボガド油、菜種油、米油、落花生油、コーン油、小麦胚芽油、大豆油、エゴマ油、綿実油、ヒマワリ種子油、カポック油、月見草油、シア脂、サル脂、カカオ脂、ゴマ油、サフラワー油、オリーブ油等を挙げることができ、動物油脂としては、例えば、豚脂、乳脂、魚油、牛脂等を挙げることができ、さらに、これらを分別、水素添加、エステル交換等により加工した油脂（例えば、硬化油）も挙げることができる。言うまでもなく、中鎖脂肪酸トリグリセリド（ＭＣＴ）、脂肪酸の部分グリセリド、リン脂質等も使用しうる。これらは単独で用いても、２種以上を併用してもよい。
中鎖脂肪酸トリグリセリドとしては、例えば、脂肪酸の炭素数が各々６〜１２、好ましくは８〜１２のトリグリセリド等を挙げることができる。また、脂肪酸の部分グリセリドとしては、例えば、脂肪酸の炭素数が各々６〜１８、好ましくは６〜１２のモノグリセリドやジグリセリド等を挙げることができる。さらに、リン脂質としては、例えば、レシチン等が挙げられる。
上記油脂のうち、取り扱い易さ、臭気等の面から、植物油脂、合成油脂や加工油脂が好ましい。これらは油脂の価格、還元型補酵素Ｑ_１０の安定性や、補酵素Ｑ_１０の溶解性等を考慮して選定するのが好ましい。例えば、ヤシ油、パーム油、パーム核油、菜種油、米油、大豆油、綿実油、ＭＣＴ等が好ましく、米油、大豆油、菜種油、ＭＣＴ等がより好ましい。なお、補酵素Ｑ_１０の溶解性や生体での吸収性の観点からは、ＭＣＴを特に好適に使用することができる。
なお、本発明の第一及び第二で前述したように、オリーブ油による還元型補酵素Ｑ_１０の安定化効果は、他の油脂による安定化効果に比べて若干劣ってはいるが、ポリグリセリン脂肪酸エステルによる還元型補酵素Ｑ_１０の生体での吸収性向上効果が、ＴｗｅｅｎやＳｐａｎによるそれと比べて著しく高く、且つポリグリセリン脂肪酸エステルによる還元型補酵素Ｑ_１０の安定化阻害が、ＴｗｅｅｎやＳｐａｎによる安定化阻害に比べて極めて小さい。このことから、油脂としてオリーブ油を用いた場合においても、上記オリーブ油の若干の難点を相殺して余りある還元型補酵素Ｑ_１０の生体での吸収性の改善効果が得られる。この観点から、本発明の第三においては、オリーブ油も好適な油脂として充分に使用しうる。
上記ポリオールとしては、例えば、グリセリン、プロピレングリコール、ポリエチレングリコール（好ましくは分子量３００〜１０００のポリエチレングリコール）等の、食用又は医薬用に有用で安全なポリオールを使用するのが好ましい。これらは単独で用いても、２種以上を併用してもよい。特にグリセリンを好ましく使用しうる。
上記油脂、上記ポリオールは、それぞれ単独でも使用できるし、上記油脂同士の混合物、上記ポリオール同士の混合物、或いは、油脂及びポリオールの混合物としても使用しうる。
上記組成物においては、上記の油脂とポリオールの量比は、特に制限されないが、補酵素Ｑ_１０の溶解性も考慮して、油脂／（油脂＋ポリオール）の重量比として、通常１／１０以上、好ましくは１／５以上、より好ましくは１／２以上、さらに好ましくは２／３以上である。言うまでもなく、ポリオールを含まない場合も好適である。
さらに、用途により、例えば栄養成分等として、アスコルビン酸類や、アスコルビン酸類を含有したレモンやオレンジ、グレープフルーツ等の果汁濃縮物（エキス、パウダー等）をさらに添加することもできる。この場合には、還元型補酵素Ｑ_１０の安定性向上の観点より、油脂としてリン脂質又はリン脂質を含有した油脂を用いることが好適であり、リン脂質は液状であることが好ましい。
アスコルビン酸類としては、特に制限されないが、例えば、アスコルビン酸、ｒｈａｍｎｏ−アスコルビン酸、ａｒａｂｏ−アスコルビン酸、ｇｌｕｃｏ−アスコルビン酸、ｆｕｃｏ−アスコルビン酸、ｇｌｕｃｏｈｅｐｔｏ−アスコルビン酸、ｘｙｌｏ−アスコルビン酸、ｇａｌａｃｔｏ−アスコルビン酸、ｇｕｌｏ−アスコルビン酸、ａｌｌｏ−アスコルビン酸、ｅｒｙｔｈｒｏ−アスコルビン酸、６−デスオキシアスコルビン酸に類するものを含み、さらに、それらのエステル体や塩であっても良い。これらは、Ｌ体、Ｄ体、或いは、ラセミ体であっても良い。また、これらは単独で用いても、２種以上を併用してもよい。
具体的には、例えば、Ｌ−アスコルビン酸、Ｌ−アスコルビン酸パルミチン酸エステル、Ｌ−アスコルビン酸ステアリン酸エステル、Ｌ−アスコルビン酸２パルミチン酸エステル、Ｌ−アスコルビン酸ナトリウム、Ｌ−アスコルビン酸カルシウム、Ｄ−ａｒａｂｏ−アスコルビン酸等を挙げることができる。油脂及び／又はポリオールへの溶解性を考慮すると、Ｌ−アスコルビン酸パルミチン酸エステル、Ｌ−アスコルビン酸ステアリン酸エステル、Ｌ−アスコルビン酸２パルミチン酸エステルが好ましい。
上記アスコルビン酸類の含有量は特に制限されないが、経済性も考慮し、還元型補酵素Ｑ_１０を除いた系を基準として、通常３０重量％以下、好ましくは２０重量％以下、より好ましくは１０重量％以下、さらに好ましくは５重量％以下である。
また、アスコルビン酸類やアスコルビン酸類を含有した果汁濃縮物を添加する場合は、ポリグリセリン脂肪酸エステル以外の界面活性剤（乳化剤）として、さらにＴｗｅｅｎやＳｐａｎを添加しても、前述したＴｗｅｅｎやＳｐａｎの共存による還元型補酵素Ｑ_１０の安定化阻害が緩和されるため、還元型補酵素Ｑ_１０の安定化と生体での高吸収性を両立した組成物とすることができる。
この場合、ポリグリセリン脂肪酸エステル以外の界面活性剤（乳化剤）としてのＴｗｅｅｎやＳｐａｎ等の含有量も特に制限されないが、還元型補酵素Ｑ_１０を除いた系を基準として、通常９０重量％以下、好ましくは７０重量％以下、より好ましくは５０重量％以下、さらに好ましくは３０重量％以下、特に好ましくは１０重量％以下である。
本発明の組成物における油脂及び／又はポリオールの含有率は、上記のようにアスコルビン酸を添加する場合、還元型補酵素Ｑ_１０を除いた系を基準として、通常１０重量％以上、好ましくは３０重量％以上、より好ましくは５０重量％以上である。アスコルビン酸類を添加しない場合は、油脂及び／又はポリオールの含有率が高いものが好ましく用いられうる。当該含有率としては、特に制限されないが、補酵素Ｑ_１０を除いた系を基準として、５０重量％以上、好ましくは６０重量％以上、より好ましくは７０重量％以上、さらに好ましくは８０重量％以上、特に好ましくは８５重量％以上である。
上記ポリグリセリン脂肪酸エステルを含有する組成物は、当該組成物を水と混合した場合（例えば、上記組成物５０ｇと水５０ｇとを混合した場合）、強撹拌することなしに（例えば、ガラス棒でかき混ぜる程度で）、乳化状態を呈する自己乳化型の組成であることが好ましい。また、ポリグリセリン脂肪酸エステルの種類と、油脂類等の他の内容物の種類や量比を選択することにより、上記目的（還元型補酵素Ｑ_１０の安定化と、生体での高吸収性）を達成することができる。
本発明の第三における還元型補酵素Ｑ_１０の安定化の程度は、特に制限されないが、例えば、還元型補酵素Ｑ_１０と油脂及び／又はポリオールのみからなる組成物を、空気中、４０℃、遮光条件下に３日間保存した後の還元型補酵素Ｑ_１０保持率を１００％として、ポリグリセリン脂肪酸エステルをさらに含有する組成物を同条件で保存した場合に、７０％以上、好ましくは８０％以上、より好ましくは９０％以上の保持率を示すものであるのが好ましい。又、前述のごとく、還元型補酵素Ｑ_１０の安定化を実質的に阻害しない組成物が望ましいことは言うまでもない。
以上のようにして、本発明の第三では、還元型補酵素Ｑ_１０の安定化と、生体での高吸収性を両立することができる。
なお、本発明の第三におけるその他の好適な要件として、前述の本発明の第一及び第二の要件を適用しても良い。
ここで本発明の第一、第二及び第三において、還元型補酵素Ｑ_１０の含有量は特に制限されないが、還元型補酵素Ｑ_１０の安定性や使用の容易さ・便利さ等を考慮して、組成物全量に対して、例えば、通常３重量％超、好ましくは５重量％超、より好ましくは６重量％超、さらに好ましくは７重量％超、特に好ましくは８重量％超である。上限は特に制限されないが、液性状等を考慮して、通常５０重量％以下、好ましくは３０重量％以下、より好ましくは２０重量％以下である。
なお、本発明の組成物は、外部添加した還元型補酵素Ｑ_１０を含有する組成物であっても良い。また、上記の油脂及び／又はポリオール中で、或いは、ポリグリセリン脂肪酸エステルを含有する油脂及び／又はポリオール中で、亜ジチオン酸ナトリウム（次亜硫酸ナトリウム）、アスコルビン酸類等の還元剤を用いて、酸化型補酵素Ｑ_１０を還元することにより得られた還元型補酵素Ｑ_１０を含有する組成物であっても良いが、実質的に、酸化型補酵素Ｑ_１０の還元に用いた還元剤の酸化物が共存しないことが好ましい。
通常は、組成物の成分が単純化でき、調製も容易であることから、還元型補酵素Ｑ_１０が外部添加された組成物、即ち、別途製造された還元型補酵素Ｑ_１０を用いて製造された組成物が好ましい。
また、本発明の組成物は、下記経口投与形態に加工する場合、常温或いはそれ以上の温度で液状（溶液のみならず、懸濁状或いはスラリーの形態も含む）であるのがより好ましい。
本発明の上記組成物は、そのまま使用することもできるが、それをカプセル剤（ハードカプセル、ソフトカプセル）、錠剤、シロップ、飲料等の経口投与形態に加工して好ましく使用しうるし、クリーム、坐薬、練り歯磨き等のための形態に加工しても使用しうる。特に好ましくは、カプセル剤であり、とりわけ、ソフトカプセルである。カプセル基材としては特に制限されず、牛骨、牛皮、豚皮、魚皮等を由来とするゼラチンをはじめとして、他の基材（例えば、食品添加物として使用しうるカラギーナン、アルギン酸等の海藻由来品やローカストビーンガムやグアーガム等の植物種子由来品等の増粘安定剤やセルロース類を含む製造用剤）も使用しうる。
また、カプセルは、ビン、ボトル、プラスチック袋、アルミラミネート袋等に入れて包装することができ、ＰＴＰ包装、３方シール包装、４方シール包装、ストリップ包装、アルミ成形包装、スティック包装等とすることができる。
本発明の効果を最大限に発揮するためには、例えば、窒素雰囲気等の不活性ガス雰囲気等の脱酸素雰囲気において、本発明の方法を実施するのが好ましく、また、本発明の組成物を調製及び／又は保存するのが好ましい。上記の加工や加工後の保存も、上記の不活性ガス雰囲気等の脱酸素雰囲気に行うのが好ましい。
以上の組成、調製方法を採用することにより、油脂及び／又はポリオールが有する酸化防護効果は実質的に阻害されず、油脂及び／又はポリオール以外の成分を含まない組成物に比して、本発明の第一及び第二においては、還元型補酵素Ｑ_１０の保持率が９５％以上、好ましくは９６％以上、より好ましくは９７％以上の組成物を得ることが期待でき、また、本発明の第三においては、還元型補酵素Ｑ_１０の保持率が７０％以上、好ましくは８０％以上、より好ましくは９０％以上の組成物を得ることが期待できる。
本発明によれば、還元型補酵素Ｑ_１０を酸化から好適に防護することができ、また、デヒドロアスコルビン酸類等の還元剤の酸化物が共存しない組成物を提供することができる。さらに、還元型補酵素Ｑ_１０の高い生体吸収性を有する組成物を提供することもできる。
発明を実施するための最良の形態
以下に製造例、実施例、比較例、参考例を挙げて本発明をさらに詳しく説明するが、本発明はこれらに限定されるものではない。なお、純度及び還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の比率（重量比）は下記ＨＰＬＣ分析により求めた。
（ＨＰＬＣ分析条件）
カラム：ＳＹＭＭＥＴＲＹ Ｃ１８（Ｗａｔｅｒｓ製）２５０ｍｍ（長さ）４．６ｍｍ（内径）、移動相；Ｃ_２Ｈ_５ＯＨ：ＣＨ_３ＯＨ＝４：３（ｖ：ｖ）、検出波長；２１０ｎｍ、流速；１ｍｌ／ｍｉｎ、還元型補酵素Ｑ_１０の保持時間；９．１ｍｉｎ、酸化型補酵素Ｑ_１０の保持時間；１３．３ｍｉｎ。
（製造例１）
１００ｇの酸化型補酵素Ｑ_１０を２５℃で１０００ｇのヘプタンに溶解させた。攪拌（攪拌所要動力０．３ｋＷ／ｍ^３）しながら、還元剤として次亜硫酸ナトリウム（純度７５％以上）１００ｇに１０００ｍｌの水を加えて溶解させた水溶液を、徐々に添加し、２５℃、ｐＨ４〜６で還元反応を行った。２時間後、反応液から水相を除去し、脱気した飽和食塩水１０００ｇでヘプタン相を６回水洗した。このヘプタン相を攪拌（攪拌所要動力０．３ｋＷ／ｍ^３）しながら２℃まで冷却し、白色のスラリーを得た。なお、以上すべての操作は窒素雰囲気下で実施した。得られたスラリーを減圧ろ過し、湿結晶を冷ヘプタン、冷エタノール、冷水、冷エタノール、冷ヘプタンで順に洗浄（洗浄に用いた冷溶媒の温度は２℃）して、さらに、湿結晶を減圧乾燥（２０〜４０℃、１〜３０ｍｍＨｇ）することにより、白色の乾燥結晶９３ｇを得た（収率９２．８モル％）。得られた結晶の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比は９９．６／０．４であった。
（製造例２）
１０００ｇのエタノール中に、１００ｇの酸化型補酵素Ｑ_１０、６０ｇのアスコルビン酸を加え、７８℃にて撹拌し、還元反応を行った。３０時間後、５０℃まで冷却し、同温を保持しながらエタノール３３０ｇと水７０ｇを添加した。このエタノール溶液を撹拌（撹拌所要動力０．３ｋＷ／ｍ^３）しながら、１０℃／時間の冷却速度で２℃まで冷却し、白色のスラリーを得た。スラリーは非常に良好な流動性を示し、容易に晶析容器より払い出しが可能であった。得られたスラリーを減圧濾過し、湿結晶を冷エタノール、冷水、冷エタノールで順に洗浄（洗浄に用いた冷溶媒の温度は２℃）して、さらに、湿結晶を減圧乾燥（２０〜４０℃、１〜３０ｍｍＨｇ）することにより、白色の乾燥結晶９７ｇを得た（有姿収率９７モル％）。なお、以上すべての操作は窒素雰囲気下で実施した。得られた結晶の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比は９９．５／０．５であった。
（実施例１〜３、比較例１）
製造例１で得られた結晶を６重量％となるように大豆油、グリセリン及びそれらの混合物にそれぞれ添加し、４０℃、空気中、遮光条件下に３日間保存後、液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比を測定した結果と、比較のため、上記と同条件下で結晶のみを保存した場合の同比率を表１に示す。

（実施例４〜１７）
製造例１で得られた結晶を６重量％となるように表２に示す各種油脂に添加し、４０℃、空気中、遮光条件下に３日間保存後、液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比を測定した結果を表２に示す。なお、中鎖脂肪酸トリグリセリドは炭素数８の比率が６割、炭素数１０の比率が４割のものを用いた。

（比較例２）
製造例１で得られた結晶をオリーブ油に６重量％となるように添加し、４０℃、空気中、遮光条件下に３日間保存した。保存後の液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比は９２．３／７．７であった。
（実施例１８〜１９、比較例３）
製造例１で得られた結晶、大豆油及びビタミンＥの以下に示す組成の組成物を調製した。これらを、４０℃、空気中、遮光条件下に３日間保存後、液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比を測定した結果を表３に示す。
ａ）組成物中の還元型補酵素Ｑ_１０の含有率４．４２重量％
補酵素Ｑ_１０を除いた系を基準とするビタミンＥ含有率０．００重量％
ｂ）組成物中の還元型補酵素Ｑ_１０の含有率４．４２重量％
補酵素Ｑ_１０を除いた系を基準とするビタミンＥ含有率１．００重量％
ｃ）組成物中の還元型補酵素Ｑ_１０の含有率４．４２重量％
補酵素Ｑ_１０を除いた系を基準とするビタミンＥ含有率４．１１重量％

（比較例４）
製造例１で得られた結晶、大豆油及びビタミンＥの以下に示す組成の組成物を調製し、４０℃、空気中、遮光条件下に３日間保存した。
組成物中の還元型補酵素Ｑ_１０の含有率５．１９重量％
補酵素Ｑ_１０を除いた系を基準とするビタミンＥ含有率４．１１重量％
保存後の液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比は、９２．９／７．１であった。
（実施例２０〜２２、比較例５〜８）
製造例１で得られた結晶を、表４に示す油脂及び／又は界面活性剤に、６重量％となるように添加し、４０℃、空気中、遮光条件下に３日間保存後、液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比を測定した結果を表４に示す。なお、中鎖脂肪酸トリグリセリド（ＭＣＴ）は炭素数８：炭素数１０＝６：４のものを用い、界面活性剤としてのＴｗｅｅｎ８０、Ｓｐａｎ８０はともにナカライテスク製のものを用いた。

（実施例２３〜２４、比較例９〜１０）
中鎖脂肪酸トリグリセリド（ＭＣＴ、炭素数８：炭素数１０＝６：４）９０重量部と、表５に記載の界面活性剤（ジグリセリンモノオレエート：理研ビタミン製ポエムＤＯ−１００Ｖ、ジグリセリンモノラウレート：太陽化学製サンソフトＱ−１２Ｄ）１０重量部を、それぞれ撹拌混合し、製造例２で得られた結晶を３％（ｗ／ｖ）となるように４０℃で溶解した。空気中、遮光下、４０℃で３日間保存後、液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比を測定した結果を表５に示す。

（実施例２５、比較例１１〜１２）
米油８０重量部と表６に記載の界面活性剤（ジグリセリンモノオレエート：理研ビタミン製ポエムＤＯ−１００Ｖ、モノグリセリンモノオレエート：太陽化学サンソフトＮｏ．０−３０、縮合リシノール酸テトラグリセリン：サンソフトＮｏ．８１８）２０重量部をそれぞれ撹拌混合し、製造例２で得られた結晶を３％（ｗ／ｖ）となるように４０℃で溶解した。空気中、遮光下、４０℃で３日間保存後、液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比を測定した結果を表６に示す。

（実施例２６）
中鎖脂肪酸トリグリセリド（ＭＣＴ、炭素数８：炭素数１０＝６：４）８０重量部、Ｓｐａｎ８０が１０重量部、ジグリセリンモノオレエート（理研ビタミン製ポエムＤＯ−１００Ｖ）が１０重量部からなる組成物に、製造例１で得られた結晶及びアスコルビン酸パルミチン酸エステルをそれぞれ４重量％となるように添加した。４０℃、空気中、遮光条件下に３日間保存後、液中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比は９９．６／０．４であった。
（参考例１）
表７記載の油脂を添加、又は、表７記載の油脂９０重量部に表７記載のポリグリセリン脂肪酸エステル（ジグリセリンモノオレエート：理研ビタミン製ポエムＤＯ−１００Ｖ、ジグリセリンモノラウレート：太陽化学製サンソフトＱ−１２Ｄ）１０重量部を添加し混合して、それぞれ基材を調製した。この基材に製造例２で得られた結晶を３％（ｗ／ｖ）となるように窒素雰囲気下、４０℃で溶解した。得られた溶液をラットに経口で投与し、血漿中の還元型補酵素Ｑ_１０量を定量して、投与後４時間目までのＡＵＣ（血中濃度曲線下面積）を算出した。この結果を表７に示すが、この結果から、ポリグリセリン脂肪酸エステルを添加することにより、生体での吸収性が向上することがわかる。

（参考例２）
Ｔｗｅｅｎ８０に製造例２で得られた結晶を３％（ｗ／ｖ）となるように窒素雰囲気下、４０℃で溶解した。得られた溶液をラットに経口で投与し、血漿中の還元型補酵素Ｑ_１０量を定量して、投与後４時間目までのＡＵＣ（血中濃度曲線下面積）を算出したところ、２．２６μｇ／ｍｌ＊ｈであった。
（参考例３）
製造例１で得られた結晶の、中鎖脂肪酸トリグリセリド（ＭＣＴ、炭素数８：炭素数１０＝６：４）、大豆油、サフラワー油、米油に対する３０℃での溶解度を表８に示す。

（実施例２７）
製造例１で得られた結晶を６重量％になるように大豆油に添加し、常法によりゼラチンのソフトカプセル剤を得た。
（実施例２８）
製造例１で得られた結晶を６重量％になるようにエゴマ油に添加し、常法によりゼラチンのソフトカプセル剤を得た。
（実施例２９）
中鎖脂肪酸トリグリセリド（ＭＣＴ、炭素数８：炭素数１０＝６：４）及び、ジグリセリンモノオレエートの混合物に製造例２で得られた結晶を５０℃にて添加し、常法により下記成分よりなるゼラチンのソフトカプセル製剤を得た。
還元型補酵素Ｑ_１０ ６０重量部
ジグリセリンモノオレエート １００重量部
中鎖脂肪酸トリグリセリド ８４０重量部
（実施例３０）
中鎖脂肪酸トリグリセリド（ＭＣＴ、炭素数８：炭素数１０＝６：４）及び、ジグリセリンモノオレエート（理研ビタミン製ポエムＤＯ−１００Ｖ）、Ｓｐａｎ８０、アスコルビン酸パルミチン酸エステルの混合物に製造例２で得られた結晶を５０℃にて添加し、常法により下記成分よりなるゼラチンのソフトカプセル製剤を得た。
還元型補酵素Ｑ_１０ ６０重量部
ジグリセリンモノオレエート １００重量部
Ｓｐａｎ８０ １００重量部
アスコルビン酸パルミチン酸エステル ６０重量部
中鎖脂肪酸トリグリセリド ６８０重量部
（実施例３１）
中鎖脂肪酸トリグリセリド（ＭＣＴ、炭素数８：炭素数１０＝６：４）及び、レシチン、アスコルビン酸パルミチン酸エステルの混合物に製造例１で得られた結晶を５０℃にて添加し、常法により下記成分よりなるゼラチンのソフトカプセル製剤を得た。
還元型補酵素Ｑ_１０ ４０重量部
レシチン １８０重量部
アスコルビン酸パルミチン酸エステル ４０重量部
中鎖脂肪酸トリグリセリド ７４０重量部
（実施例３２）
米油、硬化油、蜜蝋（粘度調整剤）、レシチンの混合物に製造例２で得られた結晶を添加し、常法により下記成分よりなるゼラチンのソフトカプセル製剤を得た。
還元型補酵素Ｑ_１０ ６０重量部
米油 ６９０重量部
硬化油 １７０重量部
蜜蝋 ６０重量部
レシチン ２０重量部
（実施例３３）
米油及び、ジグリセリンモノオレエート（理研ビタミン製ポエムＤＯ−１００Ｖ）、硬化油、蜜蝋、レシチンの混合物に製造例２で得られた結晶を添加し、常法により下記成分よりなるゼラチンのソフトカプセル製剤を得た。
還元型補酵素Ｑ_１０ １００重量部
ジグリセリンモノオレエート ７０重量部
米油 ５８０重量部
硬化油 １７０重量部
蜜蝋 ６０重量部
レシチン ２０重量部
（実施例３４）
菜種油及び、ジグリセリンモノオレエート（理研ビタミン製ポエムＤＯ−１００Ｖ）、硬化油、蜜蝋、レシチンの混合物に製造例２で得られた結晶を添加し、常法により下記成分よりなるゼラチンのソフトカプセル製剤を得た。
還元型補酵素Ｑ_１０ １００重量部
ジグリセリンモノオレエート ３２０重量部
菜種油 ３３０重量部
硬化油 １７０重量部
蜜蝋 ６０重量部
レシチン ２０重量部
（実施例３５）
エマテック（理研ビタミン製ジグリセリンモノオレエート含有油脂）及び、硬化油、蜜蝋、レシチンの混合物に製造例２で得られた結晶を添加し、常法により下記成分よりなるゼラチンのソフトカプセル製剤を得た。
還元型補酵素Ｑ_１０ １００重量部
エマテック ６５０重量部
硬化油 １７０重量部
蜜蝋 ６０重量部
レシチン ２０重量部
（実施例３６）
中鎖脂肪酸トリグリセリド（ＭＣＴ、炭素数８：炭素数１０＝６：４）及び、ジグリセリンモノオレエート（理研ビタミン製ポエムＤＯ−１００Ｖ）、Ｓｐａｎ８０、アスコルビン酸パルミチン酸エステル、硬化油、蜜蝋、レシチンの混合物に製造例２で得られた結晶を添加し、常法により下記成分よりなるゼラチンのソフトカプセル製剤を得た。
還元型補酵素Ｑ_１０ １００重量部
ジグリセリンモノオレエート １００重量部
Ｓｐａｎ８０ １００重量部
アスコルビン酸パルミチン酸エステル １００重量部
中鎖脂肪酸トリグリセリド ３５０重量部
硬化油 １７０重量部
蜜蝋 ６０重量部
レシチン ２０重量部
（実施例３７）
実施例３０、実施例３２、実施例３４で得られたゼラチンのソフトカプセルをガラス瓶に空気存在下で密封し、遮光下、２５℃で保存した（保存開始時、ゼラチンのソフトカプセル中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比はすべて９８．５／１．５）。６ヶ月後、ゼラチンのソフトカプセル中の還元型補酵素Ｑ_１０／酸化型補酵素Ｑ_１０の重量比を調べた結果を表９に示す。

産業上の利用可能性
本発明は、上述の構成よりなるので、還元型補酵素Ｑ_１０を酸化から防護して安定に保持するための簡便且つ好適な方法並びに組成物を提供することができる。Technical field
The present invention relates to reduced coenzyme Q ₁₀ Stabilization method and reduced coenzyme Q ₁₀ It is related with the composition which can hold | maintain stably. Reduced coenzyme Q ₁₀ Is oxidized coenzyme Q ₁₀ Higher oral absorbency compared with, useful as an excellent food, functional nutritional food, food for specified health use, nutritional supplement, nutritional supplement, animal medicine, beverage, feed, cosmetics, pharmaceutical, therapeutic drug, preventive drug, etc. Compound.
Background art
Reduced coenzyme Q ₁₀ Is, for example, coenzyme Q by a conventionally known method such as synthesis, fermentation, extraction from natural products, etc. ₁₀ The reduced coenzyme Q in the effluent was obtained by chromatography. ₁₀ It is known that it can be obtained by a method of concentrating sections (Japanese Patent Laid-Open No. 10-109933). In this case, the reduced coenzyme Q ₁₀ Oxidized coenzyme Q contained in ₁₀ May be reduced using a common reducing agent such as sodium borohydride, sodium dithionite (sodium hyposulfite), etc., and then concentrated by chromatography, or reduced coenzyme Q ₁₀ Is the existing high purity coenzyme Q ₁₀ It is described in this publication that it can also be obtained by a method in which the above reducing agent is allowed to act on the above.
However, the reduced coenzyme Q obtained in this way ₁₀ Cannot necessarily be obtained in a highly pure state, for example, oxidized coenzyme Q ₁₀ It is easy to obtain as low-purity crystals, oils, and semi-solids containing impurities.
As a result of intensive studies, the present inventors have found that high-quality reduced coenzyme Q ₁₀ And a patent application was filed (Japanese Patent Applications 2002-114854, 2002-114871, 2002-114872, 2002-114873, 2002-114874, 2002-114875, 2002-114476, 2002). -114877, 2002-114878, 2002-114879).
However, reduced coenzyme Q ₁₀ Is oxidized coenzyme Q by molecular oxygen ₁₀ Which is easily oxidized and is produced by the method as described in the above patent application. ₁₀ Reduced coenzyme Q ₁₀ When processed into foods, functional nutritional foods, foods for specified health use, nutritional supplements, nutritional supplements, animal drugs, beverages, feeds, cosmetics, pharmaceuticals, therapeutic drugs, preventive drugs, etc., or their materials and compositions, and / or Or, when storing after processing, stabilization remains as an important issue. In the above processing and storage, it is extremely difficult to completely remove or block oxygen, and the remaining or mixed oxygen has a great adverse effect particularly in heating during processing and storage over a long period of time. The oxidation is performed by oxidizing coenzyme Q. ₁₀ Directly related to quality problems such as by-product.
Thus, reduced coenzyme Q ₁₀ Is a very important issue, but to date, reduced coenzyme Q ₁₀ Is not commercially available, reduced coenzyme Q ₁₀ There has been little research on methods and compositions for maintaining a stable state. Only a few examples (WO01 / 52822 pamphlet) describing the composition in which a reducing agent coexists and the production method thereof are recognized. The literature includes:
1) Reduced coenzyme Q ₁₀ , Reduced coenzyme Q ₁₀ Is oxidized coenzyme Q ₁₀ An effective amount of a reducing agent for suppressing oxidation to the enzyme, and the reduced coenzyme Q ₁₀ A composition comprising an effective amount of a surfactant or vegetable oil or mixture thereof to dissolve the reducing agent, and optionally a solvent,
2) A composition for oral administration in which the above composition is formulated into a gelatin capsule or tablet;
3) Oxidized coenzyme Q ₁₀ And reduced coenzyme Q in situ using a reducing agent ₁₀ Method for preparing the above composition containing
Is disclosed.
However, the above-mentioned WO01 / 52822 discloses reduced coenzyme Q contained in the composition. ₁₀ There is no detailed description about quality and stabilization effect. In addition, the above composition and the preparation method thereof have multiple roles in the composition (that is, oxidized coenzyme Q first. ₁₀ Reduced coenzyme Q ₁₀ As a field for the reaction to reduce to the second, and second, reduced coenzyme Q ₁₀ In order to maintain a stable state), it is very complicated and complicated.
Furthermore, it should be noted that in the above composition and the method for preparing the same, the reaction mixture is used as it is, so that it is not always safe. Specifically, oxidized coenzyme Q ₁₀ Reduced coenzyme Q ₁₀ Ascorbic acid is used as a reducing agent when reducing to the above, but this ascorbic acid is oxidized to produce a considerable amount of dehydroascorbic acid, 2,3-diketogulonic acid, threonic acid, oxalic acid, etc. It is a point mixed in things. Unlike ascorbic acids, dehydroascorbic acids and oxalic acid produced by decomposition are highly harmful. For example, it has been reported that the amount of lipid peroxide in the liver and kidneys is increased, the amount of antioxidants is decreased, and the amount of oxalic acid in the kidneys is increased, resulting in decreased resistance to oxidative stress and ureteral stones. Side effects such as Nutrition Research Vol. 13, 667-676 (1993) are concerned.
Reduced coenzyme Q ₁₀ JP-A-10-109933 discloses a composition containing coenzyme Q. ₁₀ A composition comprising 0.3 g (oxidized form: reduced form = 5: 95) and 6.0 ml (5.45 g) olive oil (reduced coenzyme Q in the composition) ₁₀ Content: 4.96 wt%) and coenzyme Q ₁₀ (Oxidized type: reduced type = 15: 85) A composition comprising 20 parts by weight, vitamin E 15 parts by weight and soybean oil 350 parts by weight (reduced coenzyme Q in the composition ₁₀ Content: 4.42% by weight, coenzyme Q ₁₀ Vitamin E content: 4.11% by weight) based on the system excluding the above.
However, in this publication, reduced coenzyme Q ₁₀ There is no description about the stability etc., and as a result of investigation by the present inventors, the above composition is reduced coenzyme Q. ₁₀ It has been found that the composition for stably maintaining is not necessarily preferable.
Summary of invention
In view of the above, the present invention provides a reduced coenzyme Q. ₁₀ When processing into foods containing foods, functional nutritional foods, foods for specified health use, nutritional supplements, nutritional supplements, animal drugs, beverages, feeds, cosmetics, pharmaceuticals, therapeutic drugs, preventive drugs etc. or their materials and compositions, And / or reduced coenzyme Q when stored after processing ₁₀ An object of the present invention is to provide a simple and suitable method for protecting and protecting a drug from oxidation, as well as a composition and an oral dosage form.
As a result of diligent research to solve the above problems, the present inventors have found that food, nutritional functional foods, foods for specified health use, nutritional supplements, nutrients, animal drugs, beverages, feeds, cosmetics, pharmaceuticals, therapeutic drugs, prevention Ingredients commonly used in the preparation of drugs or their materials and compositions are reduced coenzyme Q ₁₀ Of the reduced coenzyme Q, which does not necessarily act properly on the stabilization of the enzyme (ie, protection from oxidation), and further, without preparing a complicated and complicated composition. ₁₀ Has been found to be surprisingly well protected from oxidation by molecular oxygen in the presence of fats and / or polyols.
Furthermore, the coexistence and addition of Tween and Span (both of which are surfactants (emulsifiers)) widely used for the purpose of improving absorbability in the living body is achieved by reducing the above-mentioned reduced coenzyme Q with oil and / or polyol. ₁₀ The polyglycerol fatty acid ester is surprisingly difficult to inhibit the stabilizing effect of fats and oils and / or polyols due to its coexistence and addition, and is extremely suitable surfactant ( And the present invention was completed.
That is, the first of the present invention is a reduced coenzyme Q ₁₀ Is mixed with fats and oils (but excluding olive oil) and / or polyol as a main component, and reduced coenzyme Q ₁₀ A composition which does not substantially inhibit the stabilization of the reduced coenzyme Q ₁₀ Reduced coenzyme Q, which protects against oxidation ₁₀ It relates to the stabilization method.
The second of the present invention is a reduced coenzyme Q. ₁₀ , Containing fats and oils (excluding olive oil) and / or polyols, and reduced coenzyme Q ₁₀ It is related with the composition characterized by not substantially inhibiting the stabilization of this.
The third aspect of the present invention is a reduced coenzyme Q. ₁₀ A reduced coenzyme Q, comprising a polyglycerin fatty acid ester and an oil and fat and / or a polyol ₁₀ It is related with a containing composition.
According to the present invention, the reduced coenzyme Q is stable and suitable without adding a plurality of components. ₁₀ The composition can be provided. Also, a composition suitable for recent natural orientation, that is, reduced coenzyme Q ₁₀ It is also possible to provide a composition prepared (processed) using a natural substrate.
Detailed Disclosure of the Invention
Hereinafter, the present invention will be described in detail. In this specification, coenzyme Q ₁₀ In the case where only these are described, regardless of the oxidized type or the reduced type, when both are present, it represents the entire mixture.
First, the first and second aspects of the present invention will be described.
The first of the present invention is reduced coenzyme Q ₁₀ Is mixed with fats and oils (but excluding olive oil) and / or polyol as a main component, and reduced coenzyme Q ₁₀ A composition which does not substantially inhibit the stabilization of the reduced coenzyme Q ₁₀ Reduced coenzyme Q protects against oxidation ₁₀ This is a stabilization method.
The second of the present invention is a reduced coenzyme Q. ₁₀ , Containing fats and oils (excluding olive oil) and / or polyols, and reduced coenzyme Q ₁₀ It is a composition that does not substantially inhibit the stabilization of.
Thus, in the first and second aspects of the present invention, reduced coenzyme Q by molecular oxygen is used. ₁₀ Oxidized coenzyme Q ₁₀ Oils and / or polyols are used in order to suppress the oxidation to.
In the present invention, reduced coenzyme Q ₁₀ Is reduced coenzyme Q ₁₀ It can be used alone or oxidized coenzyme Q ₁₀ It may be a mixture with. In the case of the above mixture, reduced coenzyme Q ₁₀ Of coenzyme Q ₁₀ (Ie reduced coenzyme Q ₁₀ And oxidized coenzyme Q ₁₀ Is not particularly limited, but is, for example, 20% by weight or more, preferably 40% by weight or more, more preferably 60% by weight or more, further preferably 80% by weight or more, particularly preferably 90% by weight or more, Most preferably, it is 96 weight% or more. Although an upper limit is 100 weight% and is not specifically limited, Usually, it is 99.9 weight% or less.
The fats and oils and / or polyols are preferably edible or pharmaceutical.
The fats and oils may be natural fats and oils from animals and plants, or synthetic fats and processed fats and oils. Examples of vegetable oils include palm oil, palm oil, palm kernel oil, linseed oil, camellia oil, brown rice germ oil, avocado oil, rapeseed oil, rice oil, peanut oil, corn oil, wheat germ oil, soybean oil, sesame oil , Cottonseed oil, sunflower seed oil, kapok oil, evening primrose oil, shea fat, monkey fat, cocoa butter, sesame oil, safflower oil, etc. Examples of animal fats include pork fat, milk fat, fish oil, and beef tallow Furthermore, the fats and oils (for example, hardened oil) which processed these by fractionation, hydrogenation, transesterification, etc. can also be mentioned. Needless to say, medium-chain fatty acid triglycerides (MCT), fatty acid partial glycerides, phospholipids, and the like can also be used. These may be used alone or in combination of two or more.
Examples of the medium-chain fatty acid triglyceride include triglycerides having 6 to 12, preferably 8 to 12 carbon atoms in the fatty acid. Examples of the fatty acid partial glycerides include monoglycerides and diglycerides having 6 to 18 carbon atoms, preferably 6 to 12 carbon atoms. Furthermore, examples of phospholipids include lecithin.
Among the oils and fats, vegetable oils, synthetic oils and processed oils and fats are preferable from the viewpoints of ease of handling and odor. These are the oil price, reduced coenzyme Q ₁₀ Stability and coenzyme Q ₁₀ It is preferable to select in consideration of the solubility of the resin. For example, palm oil, palm oil, palm kernel oil, rapeseed oil, rice oil, soybean oil, cottonseed oil, MCT and the like are preferable, and rice oil, soybean oil, rapeseed oil, MCT and the like are more preferable. Coenzyme Q ₁₀ MCT can be used particularly preferably from the viewpoint of the solubility of the drug and the absorbability in the living body.
Reduced coenzyme Q ₁₀ Olive oil is slightly inferior to other fats and oils in terms of its stabilizing effect (oxidation protective effect).
As the polyol, it is preferable to use a safe and useful polyol for food or medicine, such as glycerin, propylene glycol, polyethylene glycol (preferably polyethylene glycol having a molecular weight of 300 to 1000). These may be used alone or in combination of two or more. In particular, glycerin can be preferably used.
The fats and oils and the polyol can be used alone, or can be used as a mixture of the fats and oils, a mixture of the polyols or a mixture of the fats and polyols.
In the above composition, the amount ratio of the above fat and polyol is not particularly limited. ₁₀ The weight ratio of oil / fat / (oil / fat + polyol) is usually 1/10 or more, preferably 1/5 or more, more preferably 1/2 or more, and further preferably 2/3 or more. . Needless to say, it is also suitable when no polyol is contained.
Further, the above composition comprises reduced coenzyme Q. ₁₀ The oil and fat and / or polyol is the main component, but those having a high content of the oil and / or polyol can be preferably used. The content is not particularly limited, but coenzyme Q ₁₀ 50% by weight or more, preferably 60% by weight or more, more preferably 70% by weight or more, still more preferably 80% by weight or more, particularly preferably 85% by weight or more, based on the system excluding
In the present specification, “coenzyme Q” ₁₀ Is based on the total weight of the composition. ₁₀ It is based on the weight obtained by subtracting the weight of.
In the above composition, reduced coenzyme Q ₁₀ Is generally dissolved or suspended, but depending on the type of fat or polyol used, the composition may take the form of a liquid, a solid or a slurry.
Further, the above composition comprises reduced coenzyme Q. ₁₀ , Oils and / or polyols only, or further containing other components. In addition, when other components are contained, reduced coenzyme Q by fats and oils and / or polyols ₁₀ It is preferable to use a composition that does not substantially inhibit the stabilization.
For example, vitamin E is a component that is commonly used as a stabilizer or antioxidant. However, as in the composition described in JP-A-10-109933, a large amount (coenzyme Q) is used. ₁₀ 4) by weight, and the reduced coenzyme Q ₁₀ It was confirmed to inhibit the stabilization of. Therefore, vitamin E is not an essential component in the present invention. When vitamin E is used depending on the use of the composition, coenzyme Q ₁₀ Should be minimized to less than 4% by weight based on the system excluding.
For example, as described above, coexistence of Tween and Span as a surfactant (emulsifier) ₁₀ It was also confirmed to inhibit the stabilization of. Therefore, these are not essential components in the present invention. Depending on the use of the composition, when these are used, the minimum amount required, eg coenzyme Q ₁₀ The total amount of Tween and Span is preferably limited to 30% by weight or less, preferably 20% by weight or less, more preferably 10% by weight or less, based on the system excluding.
Needless to say, reduced coenzyme Q ₁₀ Ingredients that do not substantially inhibit the stabilization of, or in amounts that do not substantially inhibit, can be tolerated, and there will be many such ingredients. From this point of view, the present invention described above is directed to reducing coenzyme Q. ₁₀ The main component consists of fats and oils (except olive oil) and / or polyols, and reduced coenzyme Q ₁₀ It is defined as the essence of the invention that the composition does not substantially inhibit the stabilization. Needless to say, the simplest structure of the present invention is the reduced coenzyme Q. ₁₀ And a composition comprising only oil and fat and / or polyol, and reduced coenzyme Q by adopting the composition ₁₀ It is a method to stabilize.
Here, “reduced coenzyme Q ₁₀ The phrase “does not substantially inhibit the stabilization of” means that components other than fat and / or polyol do not impair the oxidation protection effect inherent to fat and / or polyol by more than 5%. That is, reduced coenzyme Q ₁₀ And a reduced coenzyme Q after storing a composition consisting only of oil and fat and / or polyol in air at 40 ° C. under light-shielding conditions for 3 days ₁₀ When the retention rate is 100% and the composition further added with components other than fats and / or polyols is stored under the same conditions, the retention rate is 95% or more, preferably 96% or more, more preferably 97% or more. Indicates to show.
In the first and second aspects of the present invention, a component having a reducing action may be added depending on the purpose. However, unlike the conventional composition, the reduced coenzyme Q is also used in a composition excluding the reducing agent. ₁₀ Can be kept stable.
Next, the third aspect of the present invention will be described. The third aspect of the present invention is a reduced coenzyme Q. ₁₀ , Polyglycerin fatty acid ester, and reduced coenzyme Q, containing oil and fat and / or polyol ₁₀ It is a containing composition.
In the third aspect of the present invention, reduced coenzyme Q by molecular oxygen is used. ₁₀ To oxidized coenzyme Q ₁₀ Polyglycerin as a surfactant (emulsifier) capable of sufficiently retaining the stabilizing effect (oxidation protective effect) by the above oil and fat and / or polyol. Fatty acid esters are used. Polyglycerin fatty acid ester is a kind of glycerin fatty acid ester, but unlike other glycerin fatty acid esters such as monoglycerin fatty acid ester (including organic acid monoglyceride) and polyglycerin condensed ricinoleic acid ester, it is reduced. Type coenzyme Q ₁₀ It is possible to achieve both stabilization of the body and high absorbability in the living body.
In the present invention, reduced coenzyme Q ₁₀ Is reduced coenzyme Q ₁₀ It can be used alone or oxidized coenzyme Q ₁₀ It may be a mixture with. In the case of the above mixture, reduced coenzyme Q ₁₀ Of coenzyme Q ₁₀ (Ie reduced coenzyme Q ₁₀ And oxidized coenzyme Q ₁₀ Is not particularly limited, but is, for example, 20% by weight or more, preferably 40% by weight or more, more preferably 60% by weight or more, further preferably 80% by weight or more, particularly preferably 90% by weight or more, Most preferably, it is 96 weight% or more. Although an upper limit is 100 weight% and is not specifically limited, Usually, it is 99.9 weight% or less.
The polyglycerin fatty acid ester that can be used in the present invention has the formula (1)

It is represented by In said formula (1), n represents the integer of 1-29. Each R independently represents a fatty acid residue having 2 to 22 carbon atoms or a hydrogen atom, but not all R are hydrogen atoms. That is, in the polyglycerol fatty acid ester represented by the above formula (1), the number of fatty acid residues is not particularly limited as long as it is 1 or more.
Preferably, the ratio of the number of fatty acid residues in the polyglycerol fatty acid ester / degree of polymerization of glycerol is about 1/4 to about 1/2. Here, the polymerization degree of glycerin represents the number of molecules of polymerized glycerin. For example, in the case of diglycerin monocaprylate, the number of fatty acid residues is 1 (mono) and the degree of polymerization of glycerin is 2 (di), so the above ratio is ½. In addition, when two or more fatty acid residues are present in the formula (1), each fatty acid residue may be the same or different, but generally the same is easily available. From the viewpoint of the above.
The polyglycerin fatty acid ester is not particularly limited, but reduced coenzyme Q ₁₀ In consideration of the stability and absorbability of the HLB, the lower limit of HLB is usually 4 or more, preferably 5 or more, more preferably 6 or more, more preferably 7 or more, particularly preferably 8 or more, and the upper limit. Usually, it is 12 or less, preferably 11 or less, more preferably 10 or less.
Specific examples of the polyglycerol fatty acid ester include, for example, diglycerol monocaprylate, diglycerol dicaprylate, diglycerol tricaprylate, diglycerol tetracaprylate, triglycerol monocaprylate, triglycerol dicaprylate, triglycerol. Tricaprylate, triglycerin tetracaprylate, triglycerin pentacaprylate, tetraglycerin monocaprylate, tetraglycerin dicaprylate, tetraglycerin tricaprylate, tetraglycerin tetracaprylate, tetraglycerin pentacaprylate, tetraglycerin hexacaprylate Rate, pentaglycerin monocaprylate, pentaglycerin dicaprylate, pentaglycerin tricaprylate, pentaglycerin tetra Prelate, pentaglycerin pentacaprylate, pentaglycerin hexacaprylate, pentaglycerin heptacaprylate, hexaglycerin monocaprylate, hexaglycerin dicaprylate, hexaglycerin tricaprylate, hexaglycerin tetracaprylate, hexaglycerin pentacaprylate, Hexaglycerin hexacaprylate, hexaglycerin heptacaprylate, hexaglycerin octacaprylate, heptaglycerin monocaprylate, heptaglycerin dicaprylate, heptaglycerin tricaprylate, heptaglycerin tetracaprylate, heptaglycerin pentacaprylate, heptaglycerin Hexacaprylate, heptaglycerin heptacaprylate, heptaglycerin oct Caprylate, heptaglycerin nonacaprylate, octaglycerin monocaprylate, octaglycerin dicaprylate, octaglycerin tricaprylate, octaglycerin tetracaprylate, octaglycerin pentacaprylate, octaglycerin hexacaprylate, octaglycerin heptacaprylate , Octaglycerin octacaprylate, octaglycerin nonacaprylate, octaglycerin decaprylate, nonaglycerin monocaprylate, nonaglycerin dicaprylate, nonaglycerin tricaprylate, nonaglycerin tetracaprylate, nonaglycerin pentacaprylate, nona Glycerin hexacaprylate, nonaglycerin heptacaprylate, nonaglycerin octacaprylate, nonag Reserin Nonacaprylate, Nonaglycerin Decacaprylate, Nonaglycerin Undecacaprylate, Decaglycerin Monocaprylate, Decaglycerin Dicaprylate, Decaglycerin Tricaprylate, Decaglycerin Tetracaprylate, Decaglycerin Pentacaprylate, Decaglycerin Hexacaprylate, decaglycerin heptacaprylate, decaglycerin octacaprylate, decaglycerin nonacaprylate, decaglycerin decaprylate, decaglycerin undecacaprylate, decaglycerin dodecacaprylate, diglycerin monocaprate, diglycerin dicaprate , Diglycerin tricaprate, diglycerin tetracaprate, triglycerin monocaprate, triglycerin dicaprate, tri Resin Trica Plate, Triglycerin Tetra Plate, Triglycerin Trica Plate, Triglycerin Tetra Plate, Triglycerin Pen Cap Plate, Tetraglycerin Monocap Plate, Tetraglycerin Dicap Plate, Tetraglycerin Trica Plate, Tetraglycerin Tetra Plate, Tetraglycerin Pentaplate, tetraglycerin hexacaprate, pentaglycerin monocaprate, pentaglycerin dicaprate, pentaglycerin tricaprate, pentaglycerin tetracaprate, pentaglycerin pentacaprate, pentaglycerin hexacaprate, pentaglycerin heptacaplate, hexa Glycerin monocaprate, hexaglycerin dicaprate, hexaglycerin tricapre , Hexaglycerin tetracaprate, hexaglycerin pentacaprate, hexaglycerin hexacaprate, hexaglycerin heptacaplate, hexaglycerin octacaprate, heptaglycerin monocaprate, heptaglycerin dicaprate, heptaglycerintricaprate, heptaglycerintetracap Caprate, heptaglycerin pentacap plate, heptaglycerin hexacaprate, heptaglycerin heptacap plate, heptaglycerin octacaplate, heptaglycerin nonacaplate, octaglycerin monocaprate, octaglycerin dicaprate, octaglycerin tricaplate, octaglycerin tetracaplate Caprate, octaglycerin pentacaprate, octaglycerin hexacaprate, Octaglycerin heptec plate, octaglycerin octaca plate, octaglycerin nona plate, octaglycerin deca plate, nonaglycerin monocap plate, nonaglycerin dica plate, nonaglycerin trica plate, nonaglycerin tetracap plate, nonaglycerin pentacap plate, Nonaglycerin Hexaplate, Nonaglycerin Heptaca Plate, Nonaglycerin Octaplate, Nonaglycerin Nonaca Plate, Nonaglycerin Decaplate, Nonaglycerin Undecaplate, Decaglycerin Monocaprate, Decaglycerin Dicaplate, Decaglycerin Tricaplate, Decaglycerin tetracaprate, decaglycerin pentacaprate, decaglycerin hexacaprate, decagli Phosphorus heptaka plate, decaglycerin octaca plate, decaglycerin nonaka plate, decaglycerin decaplate, decaglycerin undecaplate, decaglycerin dodecaplate, diglycerin monolaurate, diglycerin dilaurate, diglycerin trilaurate, Diglycerol tetralaurate, triglycerol monolaurate, triglycerol dilaurate, triglycerol trilaurate, triglycerol tetralaurate, triglycerol trilaurate, triglycerol tetralaurate, triglycerol pentalaurate, tetraglycerol monolaurate Rate, tetraglycerol dilaurate, tetraglycerol trilaurate, tetraglycerol tetralaurate, tetraglycerol pentalaurate , Tetraglycerin hexalaurate, pentaglycerin monolaurate, pentaglycerin dilaurate, pentaglycerin trilaurate, pentaglycerin tetralaurate, pentaglycerin pentalaurate, pentaglycerin hexalaurate, pentaglycerin heptalaurate, hexaglycerin mono Laurate, hexaglycerol dilaurate, hexaglycerol trilaurate, hexaglycerol tetralaurate, hexaglycerol pentalaurate, hexaglycerol hexalaurate, hexaglycerol heptalaurate, hexaglycerol octalaurate, heptaglycerol monolaurate, hepta Glycerin dilaurate, heptaglycerin trilaurate, heptaglycerin tetralaurate, heptag Reserine pentalaurate, heptaglycerin hexalaurate, heptaglycerin heptalaurate, heptaglycerin octalaurate, heptaglycerin nonalaurate, octaglycerin monolaurate, octaglycerin dilaurate, octaglycerin trilaurate, octaglycerin tetralaurate , Octaglycerin pentalaurate, octaglycerin hexalaurate, octaglycerin heptalaurate, octaglycerin octalaurate, octaglycerin nonalaurate, octaglycerin decalarate, nonaglycerin monolaurate, nonaglycerin dilaurate, nonaglycerin tri Laurate, nonaglycerin tetralaurate, nonaglycerin pentalaurate, nonaglycerin hexalaurate Nonaglycerin heptalaurate, nonaglycerin octalaurate, nonaglycerin nonalaurate, nonaglycerin decalaurate, nonaglycerin undecalaurate, decaglycerin monolaurate, decaglycerin dilaurate, decaglycerin trilaurate, decaglycerin Tetralaurate, decaglycerin pentalaurate, decaglycerin hexalaurate, decaglycerin heptalaurate, decaglycerin octalaurate, decaglycerin nonalaurate, decaglycerin decalarate, decaglycerin undecalaurate, decaglycerin dodecalau Rate, diglycerol monomyristate, diglycerol dimyristate, diglycerol trimyristate, diglycerol tetramyristate, triglyceride Phosphorus monomyristate, triglycerol dimyristate, triglycerol trimyristate, triglycerol tetramyristate, triglycerol trimyristate, triglycerol tetramyristate, triglycerol pentamyristate, tetraglycerol monomyristate, tetraglycerol dimyristate Myristate, tetraglycerin trimyristate, tetraglycerin tetramyristate, tetraglycerin pentamyristate, tetraglycerin hexamyristate, pentaglycerin monomyristate, pentaglycerin dimyristate, pentaglycerin trimyristate, pentaglycerin tetramyristate , Pentaglycerin pentamyristate, pentaglycerin hexamyristate, pentaglycerin heptamyristate Hexaglycerin monomyristate, hexaglycerin dimyristate, hexaglycerin trimyristate, hexaglycerin tetramyristate, hexaglycerin pentamyristate, hexaglycerin hexamyristate, hexaglycerin hepta myristate, hexaglycerin octamyristate, Heptaglycerin monomyristate, heptaglycerin dimyristate, heptaglycerin trimyristate, heptaglycerin tetramyristate, heptaglycerin pentamyristate, heptaglycerin hexamyristate, heptaglycerin heptamyristate, heptaglycerin octamyristate, heptaglycerin octamyristate Nona myristate, octaglycerin monomyristate, octaglycerin dimyristate, o Tag lysine trimyristate, octaglycerin tetramyristate, octaglycerin pentamyristate, octaglycerin hexamyristate, octaglycerin hepta myristate, octaglycerin octamyristate, octaglycerin nonamylate, octaglycerin decamyristate, nonaglycerin Monomyristate, Nonaglycerin Dimyristate, Nonaglycerin Trimyristate, Nonaglycerin Tetramyristate, Nonaglycerin Pentamyristate, Nonaglycerin Hexamyristate, Nonaglycerin Heptamyristate, Nonaglycerin Octamyristate, Nonaglycerin Nonamyli State, Nonaglycerin Decamyristate, Nonaglycerin Undecamyristate, Decaglycerin Monomilli Tate, decaglycerin dimyristate, decaglycerin trimyristate, decaglycerin tetramyristate, decaglycerin pentamyristate, decaglycerin hexamyristate, decaglycerin hepta myristate, decaglycerin octamyristate, decaglycerin nonamyristate, Decaglycerin Decamyristate, Decaglycerin Undecamyristate, Decaglycerin Dodecamyristate, Diglycerin Monopalmitate, Diglycerin Dipalmitate, Diglycerin Tripalmitate, Diglycerin Tetrapalmitate, Triglycerin Monopalmitate, Tri Glycerol dipalmitate, triglycerin tripalmitate, triglycerin tetrapalmitate, triglycerin tripalmitate, triglyceride Tetrapalmitate, triglycerin pentapalmitate, tetraglycerin monopalmitate, tetraglycerin dipalmitate, tetraglycerin tripalmitate, tetraglycerin tetrapalmitate, tetraglycerin pentapalmitate, tetraglycerin hexapalmitate, pentaglycerin mono Palmitate, pentaglycerin dipalmitate, pentaglycerin tripalmitate, pentaglycerin tetrapalmitate, pentaglycerin pentapalmitate, pentaglycerin hexapalmitate, pentaglycerin heptapalmitate, hexaglycerin monopalmitate, hexaglycerin dipalmitate , Hexaglycerin tripalmitate, hexaglycerin tetrapalmitate, hexaglycerin penta Lumitate, hexaglycerin hexapalmitate, hexaglycerin heptapalmitate, hexaglycerin octapalmitate, heptaglycerin monopalmitate, heptaglycerin dipalmitate, heptaglycerin tripalmitate, heptaglycerin tetrapalmitate, heptaglycerin pentapalmitate, Heptaglycerin hexapalmitate, heptaglycerin heptapalmitate, heptaglycerin octapalmitate, heptaglycerin nonapalmitate, octaglycerin monopalmitate, octaglycerin dipalmitate, octaglycerin tripalmitate, octaglycerin tetrapalmitate, octaglycerin Pentapalmitate, octaglycerin hexapalmitate, octaglycerin hepta Lumitate, octaglycerin octapalmitate, octaglycerin nonapalmitate, octaglycerin decapalmitate, nonaglycerin monopalmitate, nonaglycerin dipalmitate, nonaglycerin tripalmitate, nonaglycerin tetrapalmitate, nonaglycerin pentapalmitate, Nonaglycerin hexapalmitate, nonaglycerin heptapalmitate, nonaglycerin octapalmitate, nonaglycerin nonapalmitate, nonaglycerin decapalmitate, nonaglycerin undecapalmitate, decaglycerin monopalmitate, decaglycerin dipalmitate, deca Glycerol tripalmitate, decaglycerin tetrapalmitate, decaglycerin pentapalmitate, decaglycerin hexapal Mitate, decaglycerin hepta palmitate, decaglycerin octapalmitate, decaglycerin nonapalmitate, decaglycerin decapalmitate, decaglycerin undecapalmitate, decaglycerin dodecapalmitate, diglycerin monostearate, diglycerin distearate , Diglycerol tristearate, diglycerol tetrastearate, triglycerol monostearate, triglycerol distearate, triglycerol tristearate, triglycerol tetrastearate, triglycerol tristearate, triglycerol tetrastearate, tri Glycerol pentastearate, tetraglycerol monostearate, tetraglycerol distearate, tetraglycerol tristearate, tetra Glycerol tetrastearate, tetraglycerol pentastearate, tetraglycerol hexastearate, pentaglycerol monostearate, pentaglycerol distearate, pentaglycerol tristearate, pentaglycerol tetrastearate, pentaglycerol pentastearate, pentaglycerol hexastearate Stearate, pentaglycerin hepta stearate, hexaglycerin monostearate, hexaglycerin distearate, hexaglycerin tristearate, hexaglycerin tetrastearate, hexaglycerin pentastearate, hexaglycerin hexastearate, hexaglycerin hepta stearate , Hexaglycerin octastearate, heptaglycerin monostearate, hepta Reserine distearate, heptaglycerin tristearate, heptaglycerin tetrastearate, heptaglycerin pentastearate, heptaglycerin hexastearate, heptaglycerin heptastearate, heptaglycerin octastearate, heptaglycerin non-stearate, octaglycerin mono Stearate, octaglycerin distearate, octaglycerin tristearate, octaglycerin tetrastearate, octaglycerin pentastearate, octaglycerin hexastearate, octaglycerin heptastearate, octaglycerin octastearate, octaglycerin nona stearate , Octaglycerin decastate, nonaglycerin monostearate, nonaglycerin Distearate, nonaglycerin tristearate, nonaglycerin tetrastearate, nonaglycerin pentastearate, nonaglycerin hexastearate, nonaglycerin heptastearate, nonaglycerin octastearate, nonaglycerin nonastereate, nonaglycerin decastate, Nonaglycerin undecasterate, decaglycerin monostearate, decaglycerin distearate, decaglycerin tristearate, decaglycerin tetrastearate, decaglycerin pentastearate, decaglycerin hexastearate, decaglycerin hepta stearate, deca Glycerin octastearate, decaglycerin nonasterate, decaglycerin decastate, decaglycerin unde Stearate, decaglycerin dodecasterate, diglycerin monooleate, diglycerin dioleate, diglycerin trioleate, diglycerin tetraoleate, triglycerin monooleate, triglycerin dioleate, triglycerin trioleate, tri Glycerin tetraoleate, triglycerin trioleate, triglycerin tetraoleate, triglycerin pentaoleate, tetraglycerin monooleate, tetraglycerin dioleate, tetraglycerin trioleate, tetraglycerin tetraoleate, tetraglycerin pentaoleate , Tetraglycerin hexaoleate, pentaglycerin monooleate, pentaglycerin dioleate, pentaglycerin trioleate, Ntagglycerol tetraoleate, pentaglycerin pentaoleate, pentaglycerin hexaoleate, pentaglycerin heptaoleate, hexaglycerin monooleate, hexaglycerin dioleate, hexaglycerin trioleate, hexaglycerin tetraoleate, hexaglycerin penta Oleate, hexaglycerin hexaoleate, hexaglycerin heptaoleate, hexaglycerin octaoleate, heptaglycerin monooleate, heptaglycerin dioleate, heptaglycerin trioleate, heptaglycerin tetraoleate, heptaglycerin pentaoleate, Heptaglycerin hexaoleate, heptaglycerin heptaoleate, heptaglycerin octaoleate, hep Tag glycerin nonaoleate, octaglycerin monooleate, octaglycerin dioleate, octaglycerin trioleate, octaglycerin tetraoleate, octaglycerin pentaoleate, octaglycerin hexaoleate, octaglycerin heptaoleate, octaglycerin octa Oleate, octaglycerin nonaoleate, octaglycerin decaoleate, nonaglycerin monooleate, nonaglycerin dioleate, nonaglycerin trioleate, nonaglycerin tetraoleate, nonaglycerin pentaoleate, nonaglycerin hexaoleate, Nonaglycerin heptaoleate, Nonaglycerin octaoleate, Nonaglycerin nonaoleate, Nonaglycerin decaoleate, Glycerin undecaoleate, decaglycerin monooleate, decaglycerin dioleate, decaglycerin trioleate, decaglycerin tetraoleate, decaglycerin pentaoleate, decaglycerin hexaoleate, decaglycerin heptaoleate, decaglycerin octa Examples thereof include oleate, decaglycerin nonaoleate, decaglycerin decaoleate, decaglycerin undecaoleate, decaglycerin dodecaoleate and the like.
Among them, diglycerol monocaprate, diglycerol monolaurate, tetraglycerol monolaurate, pentaglycerol monomyristate, pentaglycerol trimyristate, diglycerol monostearate, tetraglycerol monostearate, tetraglycerol tristearate, Tetraglycerol pentastearate, hexaglycerol monostearate, hexaglycerol distearate, hexaglycerol tristearate, hexaglycerol pentastearate, decaglycerol distearate, decaglycerol tristearate, diglycerol monooleate, diglycerol Dioleate, tetraglycerin monooleate, hexaglycerin monooleate, hexaglycerin pentaoleate, decaglycerinate Oleate, decaglycerol pentaoleate is preferable. More preferred are diglycerol monocaprate, diglycerol monolaurate, tetraglycerol monolaurate, diglycerol monooleate, diglycerol dioleate, tetraglycerol monooleate, and decaglycerol pentaoleate. More preferred are diglycerin monocaprate, diglycerin monolaurate, diglycerin monooleate, and most preferred is diglycerin monooleate.
When these polyglycerin fatty acid esters are used, as described above, unlike the case of using monoglycerin fatty acid esters (including organic acid monoglycerides), polyglycerin condensed ricinoleic acid esters, etc., reduced coenzyme Q ₁₀ Can be stably maintained in the presence of fats and oils and / or polyols.
When the composition of the present invention is used for food applications, among the polyglycerol fatty acid esters, the fatty acid residue in the polyglycerol fatty acid ester has 8 or more carbon atoms, that is, a longer chain than caprylic acid or caprylic acid. It is preferable that the fatty acid. Moreover, it is preferable that the polymerization degree of the glycerol in polyglycerol fatty acid ester is 10 or less, and the diglycerol fatty acid ester whose polymerization degree is 2 is more preferable.
The polyglycerin fatty acid ester is not particularly limited by its coexistence and addition because it is difficult to inhibit the stabilizing effect of fats and / or polyols. For example, coenzyme Q ₁₀ The lower limit is usually 1% by weight or more, preferably 2% by weight or more, more preferably 3% by weight or more, and further preferably 5% by weight or more. The amount is usually 50% by weight or less, preferably 40% by weight or less, more preferably 30% by weight or less, still more preferably 20% by weight or less, and particularly preferably 10% by weight or less. Needless to say, an amount other than the above may be contained as required.
The oil and / or polyol used in the present invention is preferably acceptable for food or medicine.
The fats and oils may be natural fats and oils from animals and plants, or synthetic fats and processed fats and oils. Examples of vegetable oils include palm oil, palm oil, palm kernel oil, linseed oil, camellia oil, brown rice germ oil, avocado oil, rapeseed oil, rice oil, peanut oil, corn oil, wheat germ oil, soybean oil, sesame oil , Cottonseed oil, sunflower seed oil, kapok oil, evening primrose oil, shea fat, monkey fat, cocoa butter, sesame oil, safflower oil, olive oil and the like. Examples of animal fats include pork fat, milk fat, fish oil, Beef tallow etc. can be mentioned, Furthermore, the fats and oils (for example, hardened oil) which processed these by fractionation, hydrogenation, transesterification, etc. can also be mentioned. Needless to say, medium-chain fatty acid triglycerides (MCT), fatty acid partial glycerides, phospholipids, and the like can also be used. These may be used alone or in combination of two or more.
Examples of the medium-chain fatty acid triglyceride include triglycerides having 6 to 12, preferably 8 to 12 carbon atoms in the fatty acid. Examples of the fatty acid partial glycerides include monoglycerides and diglycerides having 6 to 18 carbon atoms, preferably 6 to 12 carbon atoms. Furthermore, examples of phospholipids include lecithin.
Among the oils and fats, vegetable oils, synthetic oils and processed oils and fats are preferable from the viewpoints of ease of handling and odor. These are the oil price, reduced coenzyme Q ₁₀ Stability and coenzyme Q ₁₀ It is preferable to select in consideration of the solubility of the resin. For example, palm oil, palm oil, palm kernel oil, rapeseed oil, rice oil, soybean oil, cottonseed oil, MCT and the like are preferable, and rice oil, soybean oil, rapeseed oil, MCT and the like are more preferable. Coenzyme Q ₁₀ MCT can be used particularly preferably from the viewpoint of the solubility of the drug and the absorbability in the living body.
As described above in the first and second aspects of the present invention, reduced coenzyme Q using olive oil ₁₀ Although the stabilization effect is slightly inferior to the stabilization effect of other oils and fats, reduced coenzyme Q by polyglycerol fatty acid ester ₁₀ Is significantly higher than that of Tween and Span, and reduced coenzyme Q with polyglycerin fatty acid ester. ₁₀ Is much smaller than the stabilization inhibition by Tween and Span. From this, even when olive oil is used as the fat and oil, the reduced coenzyme Q is more than offset by offsetting some of the difficulties of the olive oil. ₁₀ The improvement effect of absorbability in the living body can be obtained. From this point of view, in the third aspect of the present invention, olive oil can be sufficiently used as a suitable fat.
As the polyol, it is preferable to use a safe and useful polyol for food or medicine, such as glycerin, propylene glycol, polyethylene glycol (preferably polyethylene glycol having a molecular weight of 300 to 1000). These may be used alone or in combination of two or more. In particular, glycerin can be preferably used.
The fats and oils and the polyol can be used alone, or can be used as a mixture of the fats and oils, a mixture of the polyols or a mixture of the fats and polyols.
In the above composition, the amount ratio of the above fat and polyol is not particularly limited. ₁₀ The weight ratio of oil / fat / (oil / fat + polyol) is usually 1/10 or more, preferably 1/5 or more, more preferably 1/2 or more, and further preferably 2/3 or more. . Needless to say, it is also suitable when no polyol is contained.
Furthermore, ascorbic acids and fruit juice concentrates (extracts, powders, etc.) such as lemons, oranges, and grapefruits containing ascorbic acids can also be added, for example, as nutritional components. In this case, reduced coenzyme Q ₁₀ From the viewpoint of improving the stability, it is preferable to use phospholipids or fats and oils containing phospholipids as the fats and oils, and the phospholipids are preferably liquid.
Ascorbic acid is not particularly limited, for example, ascorbic acid, rhamno-ascorbic acid, arabo-ascorbic acid, gluco-ascorbic acid, fuco-ascorbic acid, glucohepto-ascorbic acid, xyllo-ascorbic acid, galacto-ascorbic acid, It includes those similar to gulo-ascorbic acid, allo-ascorbic acid, erythro-ascorbic acid and 6-desoxyascorbic acid, and may also be an ester or salt thereof. These may be L-form, D-form, or racemate. Moreover, these may be used independently or may use 2 or more types together.
Specifically, for example, L-ascorbic acid, L-ascorbic acid palmitic acid ester, L-ascorbic acid stearic acid ester, L-ascorbic acid 2-palmitic acid ester, L-ascorbic acid sodium, L-ascorbic acid calcium, D -Arabo-ascorbic acid etc. can be mentioned. Considering the solubility in fats and oils and / or polyols, L-ascorbic acid palmitic acid ester, L-ascorbic acid stearic acid ester, and L-ascorbic acid 2-palmitic acid ester are preferable.
The content of the ascorbic acids is not particularly limited, but reduced coenzyme Q is also considered in view of economy. ₁₀ Is usually 30% by weight or less, preferably 20% by weight or less, more preferably 10% by weight or less, and still more preferably 5% by weight or less.
In addition, when adding ascorbic acid or a fruit juice concentrate containing ascorbic acid, even if Tween or Span is added as a surfactant (emulsifier) other than polyglycerin fatty acid ester, coexistence of Tween and Span described above Reduced coenzyme Q ₁₀ Of the reduced coenzyme Q ₁₀ Thus, it is possible to obtain a composition that achieves both stabilization and high absorbability in the living body.
In this case, the content of Tween or Span as a surfactant (emulsifier) other than polyglycerin fatty acid ester is not particularly limited, but reduced coenzyme Q ₁₀ Is usually 90% by weight or less, preferably 70% by weight or less, more preferably 50% by weight or less, still more preferably 30% by weight or less, and particularly preferably 10% by weight or less.
When the ascorbic acid is added as described above, the content of fat and / or polyol in the composition of the present invention is reduced coenzyme Q. ₁₀ Is usually 10% by weight or more, preferably 30% by weight or more, more preferably 50% by weight or more, based on the system excluding. When ascorbic acids are not added, those having a high content of fats and oils and / or polyols can be preferably used. The content is not particularly limited, but coenzyme Q ₁₀ 50% by weight or more, preferably 60% by weight or more, more preferably 70% by weight or more, still more preferably 80% by weight or more, particularly preferably 85% by weight or more, based on the system excluding
The composition containing the polyglycerin fatty acid ester is mixed with water (for example, when 50 g of the composition and 50 g of water are mixed) without vigorous stirring (for example, with a glass rod). A self-emulsifying composition that exhibits an emulsified state is preferable. In addition, by selecting the type of polyglycerin fatty acid ester and the type and amount ratio of other contents such as fats and oils, the above purpose (reduced coenzyme Q ₁₀ Stabilization and high absorbability in a living body).
Reduced coenzyme Q in the third aspect of the present invention ₁₀ Although the degree of stabilization of is not particularly limited, for example, reduced coenzyme Q ₁₀ And a reduced coenzyme Q after storing a composition consisting only of oil and fat and / or polyol in air at 40 ° C. under light-shielding conditions for 3 days ₁₀ When the retention rate is 100% and a composition further containing a polyglycerol fatty acid ester is stored under the same conditions, the retention rate is 70% or more, preferably 80% or more, more preferably 90% or more. Is preferred. As described above, reduced coenzyme Q ₁₀ It goes without saying that a composition that does not substantially inhibit the stabilization of is desirable.
As described above, in the third aspect of the present invention, reduced coenzyme Q ₁₀ It is possible to achieve both stabilization and high absorbability in the living body.
Note that the first and second requirements of the present invention described above may be applied as other suitable requirements in the third aspect of the present invention.
Here, in the first, second and third aspects of the present invention, reduced coenzyme Q ₁₀ The content of is not particularly limited, but reduced coenzyme Q ₁₀ In view of the stability of the composition, ease of use, convenience, etc., the total amount of the composition is, for example, usually more than 3% by weight, preferably more than 5% by weight, more preferably more than 6% by weight, still more preferably More than 7% by weight, particularly preferably more than 8% by weight. The upper limit is not particularly limited, but is usually 50% by weight or less, preferably 30% by weight or less, more preferably 20% by weight or less in consideration of liquid properties and the like.
In addition, the composition of the present invention comprises reduced coenzyme Q added externally. ₁₀ It may be a composition containing In addition, in the above fats and / or polyols or in fats and / or polyols containing polyglycerin fatty acid esters, oxidation is performed using a reducing agent such as sodium dithionite (sodium hyposulfite) or ascorbic acid. Type coenzyme Q ₁₀ Reduced coenzyme Q obtained by reducing ₁₀ May be a composition containing, but is substantially oxidized coenzyme Q ₁₀ It is preferable that the oxide of the reducing agent used for the reduction of this does not coexist.
Usually, since the components of the composition can be simplified and preparation is easy, reduced coenzyme Q ₁₀ , Ie, a reduced coenzyme Q produced separately. ₁₀ A composition produced using is preferred.
In addition, when the composition of the present invention is processed into the following oral dosage form, it is more preferable that it is liquid (including not only a solution but also a suspended or slurry form) at room temperature or higher.
The composition of the present invention can be used as it is, but it can be preferably used after being processed into oral dosage forms such as capsules (hard capsules, soft capsules), tablets, syrups, beverages, etc., creams, suppositories, kneads It can also be used by processing into a form for brushing teeth. Particularly preferred are capsules, especially soft capsules. Capsule base material is not particularly limited, and other base materials such as carrageenan and alginic acid seaweed that can be used as food additives, including gelatin derived from cow bone, cow skin, pig skin, fish skin, etc. It is also possible to use a thickening stabilizer such as a derived product, a plant seed derived product such as locust bean gum or guar gum, or a production agent containing cellulose).
Capsules can be packaged in bottles, bottles, plastic bags, aluminum laminate bags, etc., such as PTP packaging, 3-way seal packaging, 4-way seal packaging, strip packaging, aluminum molded packaging, stick packaging, etc. be able to.
In order to maximize the effects of the present invention, the method of the present invention is preferably carried out in a deoxygenated atmosphere such as an inert gas atmosphere such as a nitrogen atmosphere, and the composition of the present invention is It is preferably prepared and / or stored. The above processing and storage after processing are preferably carried out in a deoxygenated atmosphere such as the above inert gas atmosphere.
By adopting the above composition and preparation method, the oxidation protection effect of fats and oils and / or polyols is not substantially inhibited, and the present invention is compared with a composition containing no components other than fats and oils and / or polyols. In the first and second, reduced coenzyme Q ₁₀ Can be expected to obtain a composition having a retention rate of 95% or more, preferably 96% or more, more preferably 97% or more. In the third aspect of the present invention, reduced coenzyme Q ₁₀ It can be expected to obtain a composition having a retention of 70% or more, preferably 80% or more, more preferably 90% or more.
According to the present invention, reduced coenzyme Q ₁₀ Can be suitably protected from oxidation, and a composition in which an oxide of a reducing agent such as dehydroascorbic acid does not coexist can be provided. Furthermore, reduced coenzyme Q ₁₀ It is also possible to provide a composition having a high bioabsorbability.
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, the present invention will be described in more detail with reference to production examples, examples, comparative examples, and reference examples, but the present invention is not limited thereto. Purity and reduced coenzyme Q ₁₀ / Oxidized coenzyme Q ₁₀ The ratio (weight ratio) was determined by the following HPLC analysis.
(HPLC analysis conditions)
Column: SYMMETRY C18 (manufactured by Waters) 250 mm (length) 4.6 mm (inner diameter), mobile phase; C ₂ H ₅ OH: CH ₃ OH = 4: 3 (v: v), detection wavelength: 210 nm, flow rate: 1 ml / min, reduced coenzyme Q ₁₀ Retention time: 9.1 min, oxidized coenzyme Q ₁₀ Retention time; 13.3 min.
(Production Example 1)
100 g of oxidized coenzyme Q ₁₀ Was dissolved in 1000 g of heptane at 25 ° C. Stirring (power required for stirring 0.3 kW / m ³ ), An aqueous solution prepared by adding 1000 ml of water to 100 g of sodium hyposulfite (purity of 75% or more) as a reducing agent was gradually added, and a reduction reaction was performed at 25 ° C. and pH 4-6. After 2 hours, the aqueous phase was removed from the reaction solution, and the heptane phase was washed 6 times with 1000 g of degassed saturated brine. Stir this heptane phase (power required for stirring 0.3 kW / m ³ ) To 2 ° C. to obtain a white slurry. All the above operations were performed under a nitrogen atmosphere. The obtained slurry was filtered under reduced pressure, and the wet crystals were washed with cold heptane, cold ethanol, cold water, cold ethanol and cold heptane in this order (the temperature of the cold solvent used for washing was 2 ° C.). By drying (20 to 40 ° C., 1 to 30 mmHg), 93 g of white dry crystals was obtained (yield 92.8 mol%). Reduced coenzyme Q of the obtained crystal ₁₀ / Oxidized coenzyme Q ₁₀ The weight ratio was 99.6 / 0.4.
(Production Example 2)
100 g of oxidized coenzyme Q in 1000 g of ethanol ₁₀ 60 g of ascorbic acid was added and stirred at 78 ° C. to carry out a reduction reaction. After 30 hours, the mixture was cooled to 50 ° C., and 330 g of ethanol and 70 g of water were added while maintaining the same temperature. Stir this ethanol solution (power required for stirring 0.3 kW / m ³ ), And cooled to 2 ° C. at a cooling rate of 10 ° C./hour to obtain a white slurry. The slurry showed very good fluidity and could be easily discharged from the crystallization vessel. The obtained slurry was filtered under reduced pressure, and the wet crystals were washed with cold ethanol, cold water and cold ethanol in this order (the temperature of the cold solvent used for washing was 2 ° C.), and the wet crystals were further dried under reduced pressure (20 to 40 ° C. 1 to 30 mmHg) to obtain 97 g of white dry crystals (solid yield of 97 mol%). All the above operations were performed under a nitrogen atmosphere. Reduced coenzyme Q of the obtained crystal ₁₀ / Oxidized coenzyme Q ₁₀ The weight ratio of was 99.5 / 0.5.
(Examples 1 to 3, Comparative Example 1)
The crystals obtained in Production Example 1 were respectively added to soybean oil, glycerin and a mixture thereof so as to be 6% by weight, stored at 40 ° C. in the air under light-shielding conditions for 3 days, and then reduced in the solution. Enzyme Q ₁₀ / Oxidized coenzyme Q ₁₀ Table 1 shows the results obtained by measuring the weight ratio of and the same ratio when only crystals were stored under the same conditions as above for comparison.

(Examples 4 to 17)
The crystals obtained in Production Example 1 were added to various oils and fats shown in Table 2 so as to be 6% by weight, stored at 40 ° C. in air under light-shielding conditions for 3 days, and then reduced coenzyme Q in the liquid. ₁₀ / Oxidized coenzyme Q ₁₀ The results of measuring the weight ratio of are shown in Table 2. The medium-chain fatty acid triglycerides used had a carbon number ratio of 60% and a carbon number ratio of 40%.

(Comparative Example 2)
The crystals obtained in Production Example 1 were added to olive oil so as to be 6% by weight, and stored at 40 ° C. in air under light-shielding conditions for 3 days. Reduced coenzyme Q in the liquid after storage ₁₀ / Oxidized coenzyme Q ₁₀ The weight ratio of was 92.3 / 7.7.
(Examples 18 to 19, Comparative Example 3)
A composition having the following composition of the crystals, soybean oil and vitamin E obtained in Production Example 1 was prepared. These were stored at 40 ° C. in air under light-shielded conditions for 3 days, and then reduced coenzyme Q in the solution. ₁₀ / Oxidized coenzyme Q ₁₀ The results of measuring the weight ratio are shown in Table 3.
a) Reduced coenzyme Q in the composition ₁₀ Content of 4.42% by weight
Coenzyme Q ₁₀ Vitamin E content 0.00% by weight based on the system excluding
b) Reduced coenzyme Q in the composition ₁₀ Content of 4.42% by weight
Coenzyme Q ₁₀ Vitamin E content 1.00% by weight based on the system excluding
c) Reduced coenzyme Q in the composition ₁₀ Content of 4.42% by weight
Coenzyme Q ₁₀ Vitamin E content 4.11% by weight based on the system excluding

(Comparative Example 4)
A composition having the following composition of crystals, soybean oil and vitamin E obtained in Production Example 1 was prepared, and stored for 3 days at 40 ° C. in air under light-shielding conditions.
Reduced coenzyme Q in the composition ₁₀ Content of 5.19% by weight
Coenzyme Q ₁₀ Vitamin E content 4.11% by weight based on the system excluding
Reduced coenzyme Q in the liquid after storage ₁₀ / Oxidized coenzyme Q ₁₀ The weight ratio of was 92.9 / 7.1.
(Examples 20-22, Comparative Examples 5-8)
The crystals obtained in Production Example 1 were added to the fats and oils and / or surfactants shown in Table 4 so as to be 6% by weight, stored at 40 ° C. in air under light-shielding conditions for 3 days, and then in the liquid. Reduced coenzyme Q ₁₀ / Oxidized coenzyme Q ₁₀ The results of measuring the weight ratio are shown in Table 4. The medium chain fatty acid triglycerides (MCT) were those having 8 carbon atoms: 10 carbon atoms = 6: 4, and Tween 80 and Span 80 as surfactants were both made by Nacalai Tesque.

(Examples 23 to 24, Comparative Examples 9 to 10)
90 parts by weight of medium chain fatty acid triglyceride (MCT, carbon number 8: carbon number 10 = 6: 4) and surfactants listed in Table 5 (diglycerin monooleate: Poem DO-100V made by Riken Vitamin, diglycerin mono) 10 parts by weight of Laurate: Taiyo Kagaku Sunsoft Q-12D) were mixed with stirring, and the crystals obtained in Production Example 2 were dissolved at 40 ° C. so as to be 3% (w / v). Reduced coenzyme Q in the solution after storage for 3 days at 40 ° C in the air, in the dark ₁₀ / Oxidized coenzyme Q ₁₀ The results of measuring the weight ratio are shown in Table 5.

(Example 25, Comparative Examples 11-12)
80 parts by weight of rice oil and surfactants listed in Table 6 (diglycerin monooleate: Poem DO-100V manufactured by Riken Vitamin, monoglycerin monooleate: Taiyo Kagaku Sunsoft No. 0-30, tetraglycerin condensed ricinoleate : Sunsoft No. 818) 20 parts by weight of each was stirred and mixed, and the crystals obtained in Production Example 2 were dissolved at 40 ° C. so as to be 3% (w / v). Reduced coenzyme Q in the solution after storage for 3 days at 40 ° C in the air, in the dark ₁₀ / Oxidized coenzyme Q ₁₀ The results of measuring the weight ratio are shown in Table 6.

(Example 26)
Composition comprising 80 parts by weight of medium-chain fatty acid triglyceride (MCT, carbon number 8: carbon number 10 = 6: 4), 10 parts by weight of Span 80, and 10 parts by weight of diglycerin monooleate (Poem DO-100V manufactured by Riken Vitamin) To the product, the crystals obtained in Production Example 1 and ascorbyl palmitate were added so as to be 4% by weight, respectively. Reduced coenzyme Q in solution after storage for 3 days at 40 ° C in air under light-shielded conditions ₁₀ / Oxidized coenzyme Q ₁₀ The weight ratio was 99.6 / 0.4.
(Reference Example 1)
The fats and oils listed in Table 7 are added, or polyglycerin fatty acid esters listed in Table 7 (diglycerin monooleate: Poem DO-100V manufactured by Riken Vitamin, diglycerin monolaurate: Taiyo Kagaku) in 90 parts by weight of the fats and oils listed in Table 7. 10 parts by weight of Sunsoft Q-12D) were added and mixed to prepare substrates. The crystals obtained in Production Example 2 were dissolved in this base material at 40 ° C. in a nitrogen atmosphere so as to be 3% (w / v). The resulting solution was orally administered to rats and reduced coenzyme Q in plasma ₁₀ The amount was quantified, and AUC (area under the blood concentration curve) up to 4 hours after administration was calculated. This result is shown in Table 7. From this result, it is understood that the absorbability in the living body is improved by adding polyglycerin fatty acid ester.

(Reference Example 2)
The crystals obtained in Production Example 2 were dissolved in Tween 80 at 40 ° C. in a nitrogen atmosphere so as to be 3% (w / v). The resulting solution was orally administered to rats and reduced coenzyme Q in plasma ₁₀ When the amount was quantified and the AUC (area under the blood concentration curve) up to 4 hours after administration was calculated, it was 2.26 μg / ml * h.
(Reference Example 3)
Table 8 shows the solubility of the crystals obtained in Production Example 1 at 30 ° C. in medium chain triglyceride (MCT, carbon number 8: carbon number 10 = 6: 4), soybean oil, safflower oil, and rice oil. .

(Example 27)
The crystals obtained in Production Example 1 were added to soybean oil so as to be 6% by weight, and gelatin soft capsules were obtained by a conventional method.
(Example 28)
The crystals obtained in Production Example 1 were added to egoma oil so as to be 6% by weight, and gelatin soft capsules were obtained by a conventional method.
(Example 29)
Add the crystals obtained in Production Example 2 to a mixture of medium chain fatty acid triglyceride (MCT, carbon number 8: carbon number 10 = 6: 4) and diglycerin monooleate at 50 ° C. A soft capsule formulation of gelatin was obtained.
Reduced coenzyme Q ₁₀ 60 parts by weight
100 parts by weight of diglycerin monooleate
840 parts by weight of medium chain fatty acid triglyceride
(Example 30)
In Production Example 2 to a mixture of medium-chain fatty acid triglyceride (MCT, carbon number 8: carbon number 10 = 6: 4) and diglycerin monooleate (Poem DO-100V manufactured by Riken Vitamin), Span 80, ascorbyl palmitate The obtained crystals were added at 50 ° C., and a gelatin soft capsule preparation comprising the following components was obtained by a conventional method.
Reduced coenzyme Q ₁₀ 60 parts by weight
100 parts by weight of diglycerin monooleate
Span 80 100 parts by weight
Ascorbyl palmitate 60 parts by weight
680 parts by weight of medium chain fatty acid triglyceride
(Example 31)
Add the crystals obtained in Production Example 1 to a mixture of medium-chain fatty acid triglycerides (MCT, carbon number 8: carbon number 10 = 6: 4), lecithin, and ascorbyl palmitate at 50 ° C. A gelatin soft capsule preparation comprising the following components was obtained.
Reduced coenzyme Q ₁₀ 40 parts by weight
180 parts by weight of lecithin
40 parts by weight of ascorbyl palmitate
740 parts by weight of medium chain fatty acid triglyceride
(Example 32)
The crystal obtained in Production Example 2 was added to a mixture of rice oil, hydrogenated oil, beeswax (viscosity modifier), and lecithin, and a gelatin soft capsule formulation comprising the following components was obtained by a conventional method.
Reduced coenzyme Q ₁₀ 60 parts by weight
690 parts by weight of rice oil
170 parts by weight of hardened oil
60 parts by weight of beeswax
Lecithin 20 parts by weight
(Example 33)
A gelatin soft capsule comprising the following ingredients in a conventional manner by adding the crystals obtained in Production Example 2 to a mixture of rice oil and diglycerin monooleate (Poem DO-100V manufactured by Riken Vitamin), hydrogenated oil, beeswax and lecithin. A formulation was obtained.
Reduced coenzyme Q ₁₀ 100 parts by weight
70 parts by weight of diglycerin monooleate
580 parts by weight of rice oil
170 parts by weight of hardened oil
60 parts by weight of beeswax
Lecithin 20 parts by weight
(Example 34)
A gelatin soft capsule formulation comprising the following ingredients in a conventional manner, adding the crystals obtained in Production Example 2 to a mixture of rapeseed oil and diglycerin monooleate (Poem DO-100V manufactured by Riken Vitamin), hydrogenated oil, beeswax and lecithin. Got.
Reduced coenzyme Q ₁₀ 100 parts by weight
320 parts by weight of diglycerin monooleate
Rapeseed oil 330 parts by weight
170 parts by weight of hardened oil
60 parts by weight of beeswax
Lecithin 20 parts by weight
(Example 35)
The crystals obtained in Production Example 2 were added to a mixture of Ematec (Riken vitamin diglycerin monooleate-containing fat) and hydrogenated oil, beeswax, lecithin, and a gelatin soft capsule formulation comprising the following components was obtained by a conventional method. .
Reduced coenzyme Q ₁₀ 100 parts by weight
EMATEC 650 parts by weight
170 parts by weight of hardened oil
60 parts by weight of beeswax
Lecithin 20 parts by weight
(Example 36)
Medium chain fatty acid triglyceride (MCT, carbon number 8: carbon number 10 = 6: 4) and diglycerin monooleate (Poem DO-100V manufactured by Riken Vitamin), Span 80, ascorbyl palmitate, hydrogenated oil, beeswax, lecithin The crystals obtained in Production Example 2 were added to this mixture, and a gelatin soft capsule preparation comprising the following components was obtained by a conventional method.
Reduced coenzyme Q ₁₀ 100 parts by weight
100 parts by weight of diglycerin monooleate
Span 80 100 parts by weight
Ascorbyl palmitate 100 parts by weight
350 parts by weight of medium chain fatty acid triglyceride
170 parts by weight of hardened oil
60 parts by weight of beeswax
Lecithin 20 parts by weight
(Example 37)
The gelatin soft capsules obtained in Example 30, Example 32, and Example 34 were sealed in a glass bottle in the presence of air and stored at 25 ° C. under light shielding (at the start of storage, the reduced coenzyme in the gelatin soft capsules). Q ₁₀ / Oxidized coenzyme Q ₁₀ The weight ratio of all is 98.5 / 1.5). 6 months later, reduced coenzyme Q in gelatin soft capsule ₁₀ / Oxidized coenzyme Q ₁₀ The results of examining the weight ratio are shown in Table 9.

Industrial applicability
Since the present invention has the above-described configuration, reduced coenzyme Q ₁₀ It is possible to provide a simple and suitable method and composition for protecting and protecting the compound from oxidation.

Claims (61)

The reduced coenzyme Q _10, fats and oils as the major component (excluding olive oil) and / or mixed with a polyol, and does not substantially inhibit compositions stabilization of reduced coenzyme Q _10, reduced form coenzyme Q _10, characterized in that to protect against oxidation, stabilization method of reduced coenzyme Q _10. Fats and oils are palm oil, palm oil, palm kernel oil, linseed oil, camellia oil, brown rice germ oil, avocado oil, rapeseed oil, rice oil, peanut oil, corn oil, wheat germ oil, soybean oil, egoma oil, cottonseed oil, sunflower oil Seed oil, kapok oil, evening primrose oil, shea fat, monkey fat, cacao fat, sesame oil, safflower oil, pork fat, milk fat, fish oil, beef tallow, oil processed by separation, hydrogenation, transesterification, etc., medium chain The method according to claim 1, which is at least one of fatty acid triglycerides, fatty acid partial glycerides, and phospholipids. The method according to claim 1 or 2, wherein the polyol is at least one of glycerin, propylene glycol, and polyethylene glycol. The method according to any one of claims 1 to 3, wherein a weight ratio of oil / fat / (fat + polyol) is 1/10 or more. Its content in the case of further containing vitamin E in the composition, based on the system excluding coenzyme Q _10, A method according to any one of claims first through fourth term is less than 4 wt% . The content of the case further containing Tween and / or Span in the composition, based on the system excluding coenzyme Q _10, any of the first to fifth paragraphs claims is 30 wt% or less The method described. The content of fat and / or polyol in the composition, based on the system excluding coenzyme Q _10, A method according to any one of the first to sixth paragraph claims 50 wt% or more. The content of reduced coenzyme Q ₁₀ in the composition A method according to any of claims the first to seventh term 5 by weight percent. The method according to any one of the reduced coenzyme Q ₁₀ is the first to eighth term claims is obtained by externally added. The method according to any one of claims 1 to 9, which is performed in a deoxygenated atmosphere. The method according to any one of claims 1 to 10, wherein the oil and fat and / or polyol is acceptable for food or medicine. Reduced coenzyme Q ₁₀ retention after storage for 3 days under light-shielded conditions at 40 ° C. in air, and a composition consisting only of reduced coenzyme Q ₁₀ and fats and / or polyols after storage under the same conditions The method according to any one of claims 1 to 11, wherein the rate is 95% or more when the rate is 100%. A composition comprising reduced coenzyme Q ₁₀ , fats and oils (excluding olive oil) and / or polyol, and does not substantially inhibit the stabilization of reduced coenzyme Q ₁₀ . Fats and oils are palm oil, palm oil, palm kernel oil, linseed oil, camellia oil, brown rice germ oil, avocado oil, rapeseed oil, rice oil, peanut oil, corn oil, wheat germ oil, soybean oil, egoma oil, cottonseed oil, sunflower oil Seed oil, kapok oil, evening primrose oil, shea fat, monkey fat, cacao fat, sesame oil, safflower oil, pork fat, milk fat, fish oil, beef tallow, oil processed by separation, hydrogenation, transesterification, etc., medium chain The composition according to claim 13, which is at least one of fatty acid triglycerides, fatty acid partial glycerides, and phospholipids. The composition according to claim 13 or 14, wherein the polyol is at least one of glycerin, propylene glycol, and polyethylene glycol. 16. The composition according to any one of claims 13 to 15, wherein the weight ratio of fat / oil / (fat + polyol) is 1/10 or more. Its content in the case of further containing vitamin E in the composition, based on the system excluding coenzyme Q _10, the composition according to any one of claims 13 to 16, wherein less than 4 wt% object. The content of the case further containing Tween and / or Span in the composition, based on the system excluding coenzyme _{Q 10,} to any of 13-17 wherein claims is 30 wt% or less The composition as described. The content of fat and / or polyol in the composition, co as an enzyme Q ₁₀ the reference system excluding A composition according to any of claims the 13 to 18 wherein less than 50% by weight. The content of reduced coenzyme Q ₁₀ in the composition, the composition according to any one of the first 13 to 19 wherein the claims 5 by weight percent. In effect, the composition according to any of claims the 13 to 20 wherein the oxide of the reducing agent used for the reduction of oxidized coenzyme Q ₁₀ is not co-exist. Reduced coenzyme Q ₁₀ composition according to any range of the 13 to 21 the preceding claims external those that are added. The composition according to any one of claims 13 to 22, which is prepared or stored in a deoxygenated atmosphere. The composition according to any one of claims 13 to 23, wherein the fats and oils and / or polyols are edible or pharmaceutically acceptable. The composition according to any one of claims 13 to 24, which has been processed into an oral dosage form. 26. The composition of claim 25, wherein the form is a capsule. 27. The composition of claim 26, wherein the capsule is a soft capsule. 40 ° C., in air, reduced coenzyme Q ₁₀ retention after 3 days storage in the light-shielding conditions, said after storage reduced coenzyme Q ₁₀ and oil and / or polyol alone comprising the composition under the same conditions 28. The composition according to any one of claims 13 to 27, wherein the retention is 100% or more and 95% or more. Reduced coenzyme Q _10, polyglycerol fatty acid esters, and reduced coenzyme Q ₁₀ containing composition characterized by containing fats and / or polyols. Fats and oils are palm oil, palm oil, palm kernel oil, linseed oil, camellia oil, brown rice germ oil, avocado oil, rapeseed oil, rice oil, peanut oil, corn oil, wheat germ oil, soybean oil, egoma oil, cottonseed oil, sunflower oil Seed oil, kapok oil, evening primrose oil, shea fat, monkey fat, cacao fat, sesame oil, safflower oil, olive oil, pork fat, milk fat, fish oil, beef tallow, oil processed by separation, hydrogenation, transesterification, etc., 30. The composition of claim 29, which is at least one of medium chain fatty acid triglycerides, fatty acid partial glycerides, and phospholipids. The composition according to claim 29 or 30, wherein the polyol is at least one of glycerin, propylene glycol, and polyethylene glycol. 32. The composition according to any one of claims 29 to 31, wherein a weight ratio of fat / oil / (fat + polyol) is 1/10 or more. The content of fat and / or polyol in the composition, co as an enzyme Q ₁₀ the reference system excluding A composition according to any of claims the 29 to 32 wherein less than 50% by weight. The composition according to any one of claims 29 to 33, further comprising ascorbic acids. Ascorbic acids are ascorbic acid, rhamno-ascorbic acid, arabo-ascorbic acid, gluco-ascorbic acid, fuco-ascorbic acid, glucocohepto-ascorbic acid, xylo-ascorbic acid, galacto-ascorbic acid, gulo-ascorbic acid, allo-ascorbic acid, The composition according to claim 34, wherein the composition is at least one of acids, erythro-ascorbic acid, 6-desoxyascorbic acid, esters thereof, and salts thereof. The content of the ascorbic acids, coenzyme as an enzyme Q ₁₀ criteria the system excluding the range paragraph 34 or 35 wherein the composition according claims is 30 wt% or less. 37. The composition according to claims 34 to 36, wherein the fat is phospholipid. 38. The composition of claim 37, wherein the phospholipid is liquid. The composition according to any one of claims 34 to 38, further comprising a surfactant other than the polyglycerol fatty acid ester. The composition according to claim 39, wherein the surfactant other than the polyglycerin fatty acid ester is Tween or Span. The content of the surfactant other than polyglycerol fatty acid esters, coenzyme as an enzyme Q ₁₀ based on the system excluding the range paragraph 39 or 40 wherein the composition according claims 90 wt% or less. The content of reduced coenzyme Q ₁₀ in the composition, the composition according to any one of the first 29 to 41 wherein the claims 5 by weight percent. In effect, the composition according to any of claims the 29 to 42 wherein the oxide of the reducing agent used for the reduction of oxidized coenzyme Q ₁₀ is not co-exist. Reduced coenzyme Q ₁₀ composition according to any range of the 29 to 43 the preceding claims external those that are added. 45. The composition according to any one of claims 29 to 44, wherein the oil and fat and / or polyol is acceptable for food or medicine. The polyglycerol fatty acid ester is represented by the following formula (1);

(In the formula, each R independently represents a fatty acid residue having 2 to 22 carbon atoms or a hydrogen atom. Except for the case where all R are hydrogen atoms, n represents an integer of 1 to 29.) 46. The composition according to any one of claims 29 to 45, which is represented by: The content of the polyglycerol fatty acid ester, coenzyme as an enzyme Q ₁₀ the reference system excluding A composition according to any one of 1 at% or more by weight of claims second 29-46 wherein. The content of the polyglycerol fatty acid ester, coenzyme as an enzyme Q ₁₀ the reference system excluding A composition according to any of claims the 29 to 47 wherein more than 50 wt%. The composition according to any one of claims 29 to 48, wherein the HLB of the polyglycerol fatty acid ester is 4 to 12. The composition according to any one of claims 29 to 49, wherein a ratio of (number of fatty acid residues in polyglycerol fatty acid ester) / (degree of polymerization of glycerol) is 1/4 to 1/2. The composition according to any one of claims 29 to 50, wherein the fatty acid residue in the polyglycerol fatty acid ester has 8 or more carbon atoms, and the polymerization degree of glycerol is 10 or less. 52. The composition according to any one of claims 29 to 51, wherein the polyglycerol fatty acid ester is a diglycerol fatty acid ester. 53. The composition according to claim 52, wherein the diglycerin fatty acid ester is at least one of diglycerin monocaprate, diglycerin monolaurate, and diglycerin monooleate. 54. The composition of claim 53, wherein the diglycerin fatty acid ester is diglycerin monooleate. The composition according to any one of claims 29 to 54, which is a self-emulsifying type. The composition according to any one of claims 29 to 55, which is prepared or stored in a deoxygenated atmosphere. 57. A composition according to any of claims 29 to 56, which has been processed into an oral dosage form. 58. The composition of claim 57, wherein the form is a capsule. 59. A composition according to claim 58, wherein the capsule is a soft capsule. 60. The claim 58 or 59, wherein the capsule is packaged in a bottle, bottle, plastic bag, aluminum laminate bag, PTP packaging, three-side sealed packaging, four-side sealed packaging, strip packaging, aluminum molded packaging or stick packaging. The composition as described. Reduced coenzyme Q ₁₀ retention after storage for 3 days under light-shielded conditions at 40 ° C. in air, the composition comprising reduced coenzyme Q ₁₀ and fats and / or polyols under the same conditions The composition according to any one of claims 29 to 60, which has a retention rate of 100% and is 70% or more.